NPASS Compound

Structure

NPC120667 OpenBabel07101719172D 77 85 0 0 1 0 0 0 0 0999 V2000 -5.0767 5.8621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3615 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8730 0.8461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3615 1.9540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8730 1.1079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8461 2.4425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8461 -1.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8461 -0.4885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3073 -2.4425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4612 -2.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3073 -1.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6151 -2.4425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4612 -0.9770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7689 -0.9770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8461 1.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9228 -1.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5384 0.4885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5384 3.4195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6922 2.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6922 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5384 0.4885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5384 -1.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1534 -2.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9228 -2.4425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9228 0.4885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0767 4.8851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6151 -1.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8461 0.4885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6922 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.9995 -2.4425 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7689 -2.9310 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9228 1.4655 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5384 1.4655 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8461 1.4655 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8461 -1.4655 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3845 2.9310 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3845 -0.9770 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0767 -0.9770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9228 3.4195 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.9995 -1.4655 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6151 -2.4425 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7689 1.9540 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7689 2.9310 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.1534 -0.9770 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6151 -1.4655 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0767 2.9310 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3073 -1.4655 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7689 -0.9770 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6922 -2.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3845 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3845 1.9540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6922 1.9540 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8461 0.4885 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6922 -0.9770 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9228 4.3966 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.2306 4.3966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8456 -2.9310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7689 -3.9080 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8461 -2.4425 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0767 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8456 -0.9770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4612 -2.9310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6151 1.4655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6151 3.4195 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1534 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8461 -3.4195 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5384 -3.4195 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3073 -2.4425 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9228 -1.4655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7689 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0767 1.9540 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2306 -1.4655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2306 3.4195 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4612 -0.9770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 52 1 0 0 0 0 3 52 1 0 0 0 0 4 53 1 0 0 0 0 5 53 1 0 0 0 0 7 55 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 29 2 0 0 0 0 13 29 1 0 0 0 0 14 17 2 0 0 0 0 14 29 1 0 0 0 0 15 16 1 0 0 0 0 15 30 2 0 0 0 0 16 36 1 0 0 0 0 17 40 1 0 0 0 0 18 21 1 0 0 0 0 18 35 1 0 0 0 0 19 20 1 0 0 0 0 19 38 1 0 0 0 0 20 54 1 0 0 0 0 21 55 1 0 0 0 0 22 31 1 0 0 0 0 22 52 1 0 0 0 0 23 37 1 0 0 0 0 23 56 1 0 0 0 0 24 39 1 0 0 0 0 24 57 1 0 0 0 0 25 32 1 0 0 0 0 25 71 1 0 0 0 0 26 33 1 0 0 0 0 26 72 1 0 0 0 0 27 73 1 0 0 0 0 28 58 2 3 0 0 0 28 59 1 0 0 0 0 30 31 1 0 0 0 0 30 56 1 0 0 0 0 31 57 1 6 0 0 0 32 42 1 0 0 0 0 32 60 1 6 0 0 0 33 43 1 0 0 0 0 33 61 1 6 0 0 0 34 27 1 6 0 0 0 34 44 1 0 0 0 0 34 74 1 0 0 0 0 35 53 1 0 0 0 0 35 54 1 1 0 0 0 36 54 1 1 0 0 0 36 55 1 0 0 0 0 37 57 1 6 0 0 0 37 62 1 0 0 0 0 38 53 1 0 0 0 0 38 76 1 1 0 0 0 39 52 1 0 0 0 0 39 75 1 1 0 0 0 40 63 2 0 0 0 0 40 75 1 0 0 0 0 41 45 1 0 0 0 0 41 48 1 0 0 0 0 41 58 1 1 0 0 0 42 46 1 0 0 0 0 42 64 1 6 0 0 0 43 47 1 0 0 0 0 43 65 1 6 0 0 0 44 45 1 0 0 0 0 44 66 1 1 0 0 0 45 67 1 6 0 0 0 46 49 1 0 0 0 0 46 68 1 1 0 0 0 47 50 1 0 0 0 0 47 77 1 1 0 0 0 48 74 1 0 0 0 0 48 76 1 6 0 0 0 49 71 1 0 0 0 0 49 77 1 6 0 0 0 50 72 1 0 0 0 0 50 73 1 6 0 0 0 51 69 2 0 0 0 0 51 70 1 0 0 0 0 54 6 1 1 0 0 0 55 56 1 6 0 0 0 56 8 1 6 0 0 0 57 51 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1085.56
Volume:	1074.339
LogP:	3.609
LogD:	3.167
LogS:	-3.48
# Rotatable Bonds:	14
TPSA:	309.92
# H-Bond Aceptor:	20
# H-Bond Donor:	10
# Rings:	9
# Heavy Atoms:	20

MedChem Properties

QED Drug-Likeness Score:	0.062
Synthetic Accessibility Score:	6.708
Fsp3:	0.772
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.564
MDCK Permeability:	2.2347985577653162e-05
Pgp-inhibitor:	0.851
Pgp-substrate:	0.961
Human Intestinal Absorption (HIA):	0.753
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	80.96601867675781%
Volume Distribution (VD):	0.293
Pgp-substrate:	11.846162796020508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.027
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.078
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.105
CYP3A4-substrate:	0.058

ADMET: Excretion

Clearance (CL):	0.554
Half-life (T1/2):	0.475

ADMET: Toxicity

hERG Blockers:	0.185
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.06
AMES Toxicity:	0.112
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.395
Carcinogencity:	0.032
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.924

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC120667

Natural Product ID:	NPC120667
*Common Name:**	Acacioside C
IUPAC Name:	(3S,4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4R,5S,6R)-3-acetamido-6-[[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxymethyl]-4,5-dihydroxyoxan-2-yl]oxy-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-3-[(E)-3-phenylprop-2-enoyl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:	Acacioside C
Standard InCHIKey:	ACXXXCPCILHADS-MWYXWDNYSA-N
Standard InCHI:	InChI=1S/C57H83NO19/c1-28(59)58-41-45(67)44(66)34(27-73-50-47(43(65)33(61)26-72-50)77-49-46(68)42(64)32(60)25-71-49)74-48(41)76-38-19-20-54(6)35(53(38,4)5)18-21-55(7)36(54)16-15-30-31-22-52(2,3)39(75-40(63)17-14-29-12-10-9-11-13-29)24-57(31,51(69)70)37(62)23-56(30,55)8/h9-15,17,31-39,41-50,60-62,64-68H,16,18-27H2,1-8H3,(H,58,59)(H,69,70)/b17-14+/t31-,32-,33-,34+,35-,36+,37+,38-,39-,41+,42-,43-,44+,45+,46+,47+,48-,49-,50-,54-,55+,56+,57+/m0/s1
SMILES:	CC(=N[C@H]1[C@@H](O[C@@H]([C@H]([C@@H]1O)O)CO[C@@H]1OC[C@@H]([C@@H]([C@H]1O[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O)O)O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)C[C@H]([C@@]1([C@H]2CC(C)(C)[C@H](C1)OC(=O)/C=C/c1ccccc1)C(=O)O)O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506714
PubChem CID:	15540913
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32561	acacia tenuifolia	Species	Fabaceae	Eukaryota	n.a.	suriname rainforest	n.a.	PMID[11858750]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	4

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	13.0	ug.mL-1	PMID[482969]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	275.0	ug ml-1	PMID[482969]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	220.0	ug ml-1	PMID[482969]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	215.0	ug ml-1	PMID[482969]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	160.0	ug ml-1	PMID[482969]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC120667 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	900
0.2-0.3	2379
0.3-0.4	6106
0.4-0.5	16385
0.5-0.6	13288
0.6-0.7	2970
0.7-0.8	398
0.8-0.85	24
0.85-0.9	8
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC278272
0.963	High Similarity	NPC475649
0.9568	High Similarity	NPC475345
0.9444	High Similarity	NPC476113
0.8535	High Similarity	NPC111466
0.8481	Intermediate Similarity	NPC264270
0.8481	Intermediate Similarity	NPC40085
0.8323	Intermediate Similarity	NPC265699
0.8272	Intermediate Similarity	NPC187497
0.8272	Intermediate Similarity	NPC475599
0.8272	Intermediate Similarity	NPC113620
0.8272	Intermediate Similarity	NPC100612
0.8272	Intermediate Similarity	NPC174336
0.8221	Intermediate Similarity	NPC329657
0.821	Intermediate Similarity	NPC475527
0.8121	Intermediate Similarity	NPC69425
0.8077	Intermediate Similarity	NPC243680
0.8077	Intermediate Similarity	NPC200788
0.8063	Intermediate Similarity	NPC475513
0.8063	Intermediate Similarity	NPC473755
0.8036	Intermediate Similarity	NPC477467
0.8	Intermediate Similarity	NPC472375
0.7976	Intermediate Similarity	NPC477470
0.7976	Intermediate Similarity	NPC477472
0.7976	Intermediate Similarity	NPC477474
0.7975	Intermediate Similarity	NPC210729
0.7975	Intermediate Similarity	NPC82931
0.7975	Intermediate Similarity	NPC172365
0.7949	Intermediate Similarity	NPC145899
0.7903	Intermediate Similarity	NPC472392
0.7885	Intermediate Similarity	NPC75318
0.7885	Intermediate Similarity	NPC235772
0.7885	Intermediate Similarity	NPC280941
0.7872	Intermediate Similarity	NPC289383
0.7861	Intermediate Similarity	NPC472391
0.7849	Intermediate Similarity	NPC150893
0.7849	Intermediate Similarity	NPC295408
0.7849	Intermediate Similarity	NPC329960
0.7831	Intermediate Similarity	NPC116862
0.7826	Intermediate Similarity	NPC475892
0.7821	Intermediate Similarity	NPC76999
0.7764	Intermediate Similarity	NPC475152
0.7764	Intermediate Similarity	NPC475394
0.7764	Intermediate Similarity	NPC475584
0.7756	Intermediate Similarity	NPC73829
0.7756	Intermediate Similarity	NPC119794
0.7692	Intermediate Similarity	NPC475472
0.7627	Intermediate Similarity	NPC477471
0.7627	Intermediate Similarity	NPC477469
0.7627	Intermediate Similarity	NPC477473
0.7627	Intermediate Similarity	NPC477466
0.7616	Intermediate Similarity	NPC476784
0.7609	Intermediate Similarity	NPC471623
0.7586	Intermediate Similarity	NPC165234
0.7586	Intermediate Similarity	NPC475536
0.7568	Intermediate Similarity	NPC324251
0.7568	Intermediate Similarity	NPC471629
0.7568	Intermediate Similarity	NPC473400
0.7568	Intermediate Similarity	NPC317882
0.7568	Intermediate Similarity	NPC306001
0.7568	Intermediate Similarity	NPC471754
0.7568	Intermediate Similarity	NPC275170
0.7568	Intermediate Similarity	NPC206211
0.7556	Intermediate Similarity	NPC13989
0.7543	Intermediate Similarity	NPC475300
0.7543	Intermediate Similarity	NPC475505
0.7543	Intermediate Similarity	NPC473641
0.7543	Intermediate Similarity	NPC475464
0.7543	Intermediate Similarity	NPC473797
0.7543	Intermediate Similarity	NPC475437
0.753	Intermediate Similarity	NPC31171
0.753	Intermediate Similarity	NPC237240
0.7516	Intermediate Similarity	NPC190849
0.7516	Intermediate Similarity	NPC171007
0.7515	Intermediate Similarity	NPC472761
0.7514	Intermediate Similarity	NPC124828
0.7513	Intermediate Similarity	NPC473490
0.7513	Intermediate Similarity	NPC473558
0.75	Intermediate Similarity	NPC191193
0.75	Intermediate Similarity	NPC215892
0.75	Intermediate Similarity	NPC242662
0.75	Intermediate Similarity	NPC321072
0.7473	Intermediate Similarity	NPC453583
0.7473	Intermediate Similarity	NPC473300
0.7473	Intermediate Similarity	NPC475336
0.7472	Intermediate Similarity	NPC469420
0.7472	Intermediate Similarity	NPC102465
0.747	Intermediate Similarity	NPC61717
0.747	Intermediate Similarity	NPC244380
0.746	Intermediate Similarity	NPC181964
0.746	Intermediate Similarity	NPC471606
0.746	Intermediate Similarity	NPC208553
0.7459	Intermediate Similarity	NPC327699
0.7458	Intermediate Similarity	NPC473557
0.7458	Intermediate Similarity	NPC473468
0.7458	Intermediate Similarity	NPC475567
0.7456	Intermediate Similarity	NPC474564
0.744	Intermediate Similarity	NPC94602
0.7433	Intermediate Similarity	NPC33372
0.7433	Intermediate Similarity	NPC67246
0.7421	Intermediate Similarity	NPC471024
0.7416	Intermediate Similarity	NPC475531
0.7416	Intermediate Similarity	NPC475175
0.7416	Intermediate Similarity	NPC475198
0.7412	Intermediate Similarity	NPC476092
0.7412	Intermediate Similarity	NPC475218
0.7412	Intermediate Similarity	NPC70236
0.7412	Intermediate Similarity	NPC475447
0.7405	Intermediate Similarity	NPC124878
0.7405	Intermediate Similarity	NPC231888
0.7405	Intermediate Similarity	NPC290276
0.7405	Intermediate Similarity	NPC10121
0.7405	Intermediate Similarity	NPC10883
0.7405	Intermediate Similarity	NPC204214
0.7405	Intermediate Similarity	NPC198918
0.7405	Intermediate Similarity	NPC63404
0.7405	Intermediate Similarity	NPC92283
0.7405	Intermediate Similarity	NPC35338
0.7396	Intermediate Similarity	NPC201692
0.7394	Intermediate Similarity	NPC108852
0.7394	Intermediate Similarity	NPC298469
0.7394	Intermediate Similarity	NPC193579
0.7394	Intermediate Similarity	NPC261709
0.7394	Intermediate Similarity	NPC111586
0.7391	Intermediate Similarity	NPC80599
0.7391	Intermediate Similarity	NPC209851
0.7389	Intermediate Similarity	NPC162925
0.7389	Intermediate Similarity	NPC87153
0.7381	Intermediate Similarity	NPC173934
0.7375	Intermediate Similarity	NPC473443
0.7371	Intermediate Similarity	NPC477623
0.7371	Intermediate Similarity	NPC314941
0.7362	Intermediate Similarity	NPC302276
0.7362	Intermediate Similarity	NPC180770
0.7358	Intermediate Similarity	NPC471025
0.7356	Intermediate Similarity	NPC469417
0.7353	Intermediate Similarity	NPC470274
0.7349	Intermediate Similarity	NPC298067
0.7349	Intermediate Similarity	NPC214821
0.7348	Intermediate Similarity	NPC471870
0.7347	Intermediate Similarity	NPC315889
0.7342	Intermediate Similarity	NPC28069
0.7342	Intermediate Similarity	NPC77651
0.7333	Intermediate Similarity	NPC477488
0.7326	Intermediate Similarity	NPC472548
0.7326	Intermediate Similarity	NPC477905
0.7314	Intermediate Similarity	NPC469399
0.7312	Intermediate Similarity	NPC225103
0.731	Intermediate Similarity	NPC469448
0.7308	Intermediate Similarity	NPC469421
0.7296	Intermediate Similarity	NPC147032
0.7289	Intermediate Similarity	NPC141669
0.7283	Intermediate Similarity	NPC473414
0.7283	Intermediate Similarity	NPC256142
0.7283	Intermediate Similarity	NPC304876
0.7283	Intermediate Similarity	NPC472005
0.7283	Intermediate Similarity	NPC472030
0.7283	Intermediate Similarity	NPC257213
0.7283	Intermediate Similarity	NPC242262
0.7283	Intermediate Similarity	NPC158333
0.7283	Intermediate Similarity	NPC472657
0.7283	Intermediate Similarity	NPC472022
0.7283	Intermediate Similarity	NPC237549
0.7283	Intermediate Similarity	NPC1173
0.7283	Intermediate Similarity	NPC472658
0.7283	Intermediate Similarity	NPC265395
0.7283	Intermediate Similarity	NPC249471
0.7278	Intermediate Similarity	NPC298005
0.7278	Intermediate Similarity	NPC473541
0.7278	Intermediate Similarity	NPC36463
0.7273	Intermediate Similarity	NPC162910
0.7268	Intermediate Similarity	NPC469775
0.7268	Intermediate Similarity	NPC135334
0.7268	Intermediate Similarity	NPC469773
0.7268	Intermediate Similarity	NPC295941
0.7268	Intermediate Similarity	NPC100925
0.7268	Intermediate Similarity	NPC469777
0.7268	Intermediate Similarity	NPC32723
0.7268	Intermediate Similarity	NPC469772
0.7268	Intermediate Similarity	NPC469778
0.7268	Intermediate Similarity	NPC469774
0.7268	Intermediate Similarity	NPC469776
0.7267	Intermediate Similarity	NPC475138
0.7267	Intermediate Similarity	NPC472388
0.7263	Intermediate Similarity	NPC477491
0.7262	Intermediate Similarity	NPC477468
0.7257	Intermediate Similarity	NPC477735
0.725	Intermediate Similarity	NPC315253
0.725	Intermediate Similarity	NPC230331
0.7241	Intermediate Similarity	NPC5115
0.7241	Intermediate Similarity	NPC469398
0.7241	Intermediate Similarity	NPC112523
0.7241	Intermediate Similarity	NPC228204
0.7241	Intermediate Similarity	NPC472549
0.7241	Intermediate Similarity	NPC114410
0.7241	Intermediate Similarity	NPC26033
0.7239	Intermediate Similarity	NPC472437
0.7228	Intermediate Similarity	NPC471871
0.7222	Intermediate Similarity	NPC472361
0.7219	Intermediate Similarity	NPC260194

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC120667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	510
0.2-0.3	1207
0.3-0.4	2874
0.4-0.5	3150
0.5-0.6	1081
0.6-0.7	151
0.7-0.8	12
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7943	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD8368	Discontinued
0.768	Intermediate Similarity	NPD8407	Phase 2
0.7619	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD8360	Approved
0.7609	Intermediate Similarity	NPD8361	Approved
0.7609	Intermediate Similarity	NPD8435	Approved
0.753	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD8485	Approved
0.7396	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD8320	Phase 1
0.7371	Intermediate Similarity	NPD8319	Approved
0.7136	Intermediate Similarity	NPD8151	Discontinued
0.71	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7874	Approved
0.7065	Intermediate Similarity	NPD7801	Approved
0.7062	Intermediate Similarity	NPD7699	Phase 2
0.7062	Intermediate Similarity	NPD7700	Phase 2
0.7026	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7783	Phase 2
0.698	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6823	Phase 2
0.6919	Remote Similarity	NPD7799	Discontinued
0.6915	Remote Similarity	NPD7701	Phase 2
0.6907	Remote Similarity	NPD6534	Approved
0.6907	Remote Similarity	NPD6535	Approved
0.6893	Remote Similarity	NPD8417	Discontinued
0.6893	Remote Similarity	NPD8404	Phase 2
0.6884	Remote Similarity	NPD7697	Approved
0.6884	Remote Similarity	NPD7696	Phase 3
0.6884	Remote Similarity	NPD7698	Approved
0.6878	Remote Similarity	NPD8313	Approved
0.6878	Remote Similarity	NPD8312	Approved
0.685	Remote Similarity	NPD7870	Phase 2
0.685	Remote Similarity	NPD7871	Phase 2
0.6769	Remote Similarity	NPD6213	Phase 3
0.6769	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6212	Phase 3
0.6734	Remote Similarity	NPD6777	Approved
0.6734	Remote Similarity	NPD6779	Approved
0.6734	Remote Similarity	NPD6776	Approved
0.6734	Remote Similarity	NPD6780	Approved
0.6734	Remote Similarity	NPD6778	Approved
0.6734	Remote Similarity	NPD6782	Approved
0.6734	Remote Similarity	NPD6781	Approved
0.6699	Remote Similarity	NPD8462	Phase 1
0.6682	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD8328	Phase 3
0.6598	Remote Similarity	NPD8150	Discontinued
0.6593	Remote Similarity	NPD8455	Phase 2
0.6575	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7435	Discontinued
0.6552	Remote Similarity	NPD7497	Discontinued
0.6534	Remote Similarity	NPD8323	Discontinued
0.6528	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD8059	Phase 3
0.6494	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD2613	Approved
0.6488	Remote Similarity	NPD7999	Approved
0.6488	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5981	Approved
0.6477	Remote Similarity	NPD8166	Discontinued
0.6477	Remote Similarity	NPD2575	Approved
0.6476	Remote Similarity	NPD7930	Approved
0.6471	Remote Similarity	NPD3088	Approved
0.6471	Remote Similarity	NPD3087	Approved
0.6471	Remote Similarity	NPD3614	Approved
0.6471	Remote Similarity	NPD2573	Approved
0.6471	Remote Similarity	NPD2570	Approved
0.6471	Remote Similarity	NPD3615	Approved
0.6471	Remote Similarity	NPD2566	Approved
0.6471	Remote Similarity	NPD4745	Approved
0.6471	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3089	Approved
0.6471	Remote Similarity	NPD4746	Phase 3
0.6471	Remote Similarity	NPD3090	Approved
0.6471	Remote Similarity	NPD2574	Discontinued
0.6471	Remote Similarity	NPD3616	Approved
0.6471	Remote Similarity	NPD2571	Approved
0.6467	Remote Similarity	NPD8390	Approved
0.6467	Remote Similarity	NPD8392	Approved
0.6467	Remote Similarity	NPD8391	Approved
0.6465	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7315	Approved
0.6395	Remote Similarity	NPD4684	Phase 3
0.6395	Remote Similarity	NPD4686	Approved
0.6395	Remote Similarity	NPD4685	Phase 3
0.6392	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7228	Approved
0.6386	Remote Similarity	NPD8448	Approved
0.6378	Remote Similarity	NPD5036	Approved
0.6374	Remote Similarity	NPD7715	Approved
0.6374	Remote Similarity	NPD7714	Approved
0.6355	Remote Similarity	NPD8285	Discontinued
0.6345	Remote Similarity	NPD5037	Approved
0.6345	Remote Similarity	NPD5038	Approved
0.634	Remote Similarity	NPD7240	Approved
0.6325	Remote Similarity	NPD8451	Approved
0.6322	Remote Similarity	NPD6852	Discontinued
0.6319	Remote Similarity	NPD7239	Suspended
0.6316	Remote Similarity	NPD8468	Phase 2
0.6313	Remote Similarity	NPD7236	Approved
0.6307	Remote Similarity	NPD7266	Discontinued
0.6303	Remote Similarity	NPD7827	Phase 1
0.6303	Remote Similarity	NPD7829	Approved
0.6303	Remote Similarity	NPD7830	Approved
0.6296	Remote Similarity	NPD8127	Discontinued
0.6292	Remote Similarity	NPD3400	Discontinued
0.6287	Remote Similarity	NPD8074	Phase 3
0.6284	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.628	Remote Similarity	NPD8513	Phase 3
0.628	Remote Similarity	NPD8516	Approved
0.628	Remote Similarity	NPD8515	Approved
0.628	Remote Similarity	NPD8517	Approved
0.6276	Remote Similarity	NPD5035	Approved
0.6257	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD4738	Phase 2
0.6256	Remote Similarity	NPD5030	Phase 2
0.6243	Remote Similarity	NPD5121	Approved
0.6243	Remote Similarity	NPD5119	Approved
0.6243	Remote Similarity	NPD5120	Approved
0.6237	Remote Similarity	NPD7972	Discontinued
0.6235	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD6842	Approved
0.6231	Remote Similarity	NPD6841	Approved
0.6231	Remote Similarity	NPD6843	Phase 3
0.6226	Remote Similarity	NPD3644	Approved
0.6226	Remote Similarity	NPD3643	Approved
0.6226	Remote Similarity	NPD3642	Approved
0.6225	Remote Similarity	NPD4420	Approved
0.6224	Remote Similarity	NPD36	Approved
0.6224	Remote Similarity	NPD5028	Approved
0.6224	Remote Similarity	NPD4954	Approved
0.6224	Remote Similarity	NPD5026	Approved
0.6224	Remote Similarity	NPD5034	Approved
0.6224	Remote Similarity	NPD4955	Approved
0.6223	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6677	Suspended
0.6201	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD7625	Phase 1
0.6196	Remote Similarity	NPD7458	Discontinued
0.6195	Remote Similarity	NPD7565	Approved
0.6185	Remote Similarity	NPD7961	Discontinued
0.6184	Remote Similarity	NPD5005	Approved
0.6184	Remote Similarity	NPD5006	Approved
0.6181	Remote Similarity	NPD8434	Phase 2
0.6168	Remote Similarity	NPD3132	Approved
0.6168	Remote Similarity	NPD2610	Approved
0.6168	Remote Similarity	NPD8299	Approved
0.6168	Remote Similarity	NPD4216	Approved
0.6168	Remote Similarity	NPD8341	Approved
0.6168	Remote Similarity	NPD2608	Approved
0.6168	Remote Similarity	NPD8342	Approved
0.6168	Remote Similarity	NPD4218	Approved
0.6168	Remote Similarity	NPD3131	Approved
0.6168	Remote Similarity	NPD2612	Approved
0.6168	Remote Similarity	NPD2611	Approved
0.6168	Remote Similarity	NPD2609	Approved
0.6168	Remote Similarity	NPD4217	Approved
0.6168	Remote Similarity	NPD4215	Approved
0.6168	Remote Similarity	NPD8340	Approved
0.6149	Remote Similarity	NPD8265	Approved
0.6149	Remote Similarity	NPD8133	Approved
0.6142	Remote Similarity	NPD5032	Approved
0.6139	Remote Similarity	NPD7296	Approved
0.6139	Remote Similarity	NPD6686	Approved
0.6136	Remote Similarity	NPD2567	Approved
0.6136	Remote Similarity	NPD2569	Approved
0.6131	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD2218	Phase 2
0.6121	Remote Similarity	NPD8294	Approved
0.6121	Remote Similarity	NPD2217	Approved
0.6121	Remote Similarity	NPD8377	Approved
0.6118	Remote Similarity	NPD7319	Approved
0.6111	Remote Similarity	NPD6010	Discontinued
0.6105	Remote Similarity	NPD4620	Approved
0.6105	Remote Similarity	NPD5201	Approved
0.6105	Remote Similarity	NPD5203	Approved
0.6105	Remote Similarity	NPD4617	Approved
0.6105	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD3648	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD7282	Approved
0.6096	Remote Similarity	NPD37	Approved
0.6092	Remote Similarity	NPD7713	Phase 3
0.6091	Remote Similarity	NPD5031	Approved
0.6091	Remote Similarity	NPD5029	Approved
0.6091	Remote Similarity	NPD5027	Approved
0.6085	Remote Similarity	NPD4967	Phase 2
0.6085	Remote Similarity	NPD4965	Approved
0.6085	Remote Similarity	NPD4966	Approved
0.6084	Remote Similarity	NPD8335	Approved
0.6084	Remote Similarity	NPD7503	Approved
0.6084	Remote Similarity	NPD8378	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data