NPASS Compound

Structure

NPC475454 OpenBabel07101718182D 46 51 0 0 1 0 0 0 0 0999 V2000 2.5481 -3.4327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5481 -1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4904 4.7724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9808 3.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 1.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0962 3.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2469 0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9456 0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3975 0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7950 0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 -3.4327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 2.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 3.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 2.9423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 -1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 -0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0962 1.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6987 0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 -2.9423 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6987 -1.9615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0962 0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5481 0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 -0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7950 1.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9456 2.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9423 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8494 1.4712 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8494 4.4135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8494 -1.4712 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8494 -2.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 2.4519 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9808 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.9615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5481 -0.4904 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6443 2.4519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 5.3942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 -3.4327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6987 -1.9615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9456 3.4327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 36 1 0 0 0 0 4 36 1 0 0 0 0 6 38 1 0 0 0 0 7 46 1 0 0 0 0 8 10 2 0 0 0 0 8 26 1 0 0 0 0 9 12 2 0 0 0 0 9 26 1 0 0 0 0 10 27 1 0 0 0 0 11 13 1 0 0 0 0 11 28 2 0 0 0 0 12 29 1 0 0 0 0 13 32 1 0 0 0 0 14 19 1 0 0 0 0 14 24 1 0 0 0 0 15 18 1 0 0 0 0 15 31 1 0 0 0 0 16 17 1 0 0 0 0 16 33 1 0 0 0 0 17 37 1 0 0 0 0 18 38 1 0 0 0 0 19 39 1 0 0 0 0 20 21 1 0 0 0 0 20 39 1 0 0 0 0 21 40 1 0 0 0 0 22 26 2 0 0 0 0 22 30 1 0 0 0 0 23 27 1 0 0 0 0 24 1 1 6 0 0 0 24 25 1 0 0 0 0 25 2 1 1 0 0 0 25 34 1 0 0 0 0 27 41 2 0 0 0 0 28 34 1 0 0 0 0 28 40 1 0 0 0 0 29 30 2 0 0 0 0 29 42 1 0 0 0 0 30 46 1 0 0 0 0 31 36 1 0 0 0 0 31 37 1 1 0 0 0 32 37 1 1 0 0 0 32 38 1 0 0 0 0 33 36 1 0 0 0 0 33 43 1 1 0 0 0 34 39 1 6 0 0 0 35 44 2 0 0 0 0 35 45 1 0 0 0 0 37 5 1 1 0 0 0 38 40 1 6 0 0 0 39 35 1 1 0 0 0 40 23 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	632.41
Volume:	683.343
LogP:	6.313
LogD:	5.294
LogS:	-4.681
# Rotatable Bonds:	6
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.215
Synthetic Accessibility Score:	5.11
Fsp3:	0.7
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.322
MDCK Permeability:	2.333504380658269e-05
Pgp-inhibitor:	0.085
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.47
30% Bioavailability (F30%):	0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	98.9280776977539%
Volume Distribution (VD):	0.39
Pgp-substrate:	3.171133279800415%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.728
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.786
CYP2C9-inhibitor:	0.313
CYP2C9-substrate:	0.914
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.637
CYP3A4-inhibitor:	0.464
CYP3A4-substrate:	0.543

ADMET: Excretion

Clearance (CL):	3.347
Half-life (T1/2):	0.228

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.563
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.817
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.086
Carcinogencity:	0.072
Eye Corrosion:	0.005
Eye Irritation:	0.06
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC475454

Natural Product ID:	NPC475454
*Common Name:**	Uncarinic Acid D
IUPAC Name:	(1S,2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-10-hydroxy-6a-[(Z)-4-(4-hydroxy-3-methoxyphenyl)-2-oxobut-3-enyl]-1,2,6b,9,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Synonyms:	Uncarinic acid D
Standard InCHIKey:	CEDIUSJLGQLBRO-ITVDRDEASA-N
Standard InCHI:	InChI=1S/C40H56O6/c1-24-14-19-39(35(44)45)20-21-40(23-27(41)10-8-26-9-12-29(42)30(22-26)46-7)28(34(39)25(24)2)11-13-32-37(5)17-16-33(43)36(3,4)31(37)15-18-38(32,40)6/h8-12,22,24-25,31-34,42-43H,13-21,23H2,1-7H3,(H,44,45)/b10-8-/t24-,25+,31+,32-,33+,34+,37+,38-,39+,40+/m1/s1
SMILES:	COc1cc(/C=CC(=O)C[C@@]23CC[C@@]4([C@H](C2=CC[C@H]2[C@@]3(C)CC[C@@H]3[C@]2(C)CC[C@@H](C3(C)C)O)[C@@H](C)[C@@H](CC4)C)C(=O)O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505952
PubChem CID:	44583695
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869194]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18588343]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19331340]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27700077]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28225280]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31789520]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31804070]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	6

Activity Type	# Activity
Cell Line	5
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4581	Individual Protein	Phospholipase C-gamma-1	Homo sapiens	IC50	=	44100.0	nM	PMID[489417]
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	=	39900.0	nM	PMID[489417]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	2.8	ug.mL-1	PMID[489417]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2.5	ug.mL-1	PMID[489417]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.6	ug.mL-1	PMID[489417]
NPT658	Cell Line	HT1197	Homo sapiens	IC50	=	4.4	ug.mL-1	PMID[489417]

☑ 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 NPC475454 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	349
0.1-0.2	1381
0.2-0.3	2806
0.3-0.4	5928
0.4-0.5	9711
0.5-0.6	8498
0.6-0.7	10842
0.7-0.8	2979
0.8-0.85	84
0.85-0.9	64
0.9-0.95	40
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473680
1.0	High Similarity	NPC475311
1.0	High Similarity	NPC473579
0.9861	High Similarity	NPC118033
0.9793	High Similarity	NPC475579
0.9793	High Similarity	NPC473773
0.9459	High Similarity	NPC105942
0.9459	High Similarity	NPC205392
0.9444	High Similarity	NPC307205
0.9306	High Similarity	NPC477873
0.9306	High Similarity	NPC469447
0.9178	High Similarity	NPC53520
0.9167	High Similarity	NPC27518
0.9167	High Similarity	NPC304110
0.9128	High Similarity	NPC145527
0.9128	High Similarity	NPC470619
0.9128	High Similarity	NPC208785
0.9128	High Similarity	NPC470618
0.9028	High Similarity	NPC182249
0.8986	High Similarity	NPC66894
0.8986	High Similarity	NPC8102
0.898	High Similarity	NPC25491
0.8966	High Similarity	NPC473591
0.8966	High Similarity	NPC271494
0.8966	High Similarity	NPC155192
0.8958	High Similarity	NPC471152
0.8951	High Similarity	NPC43353
0.8933	High Similarity	NPC273358
0.8933	High Similarity	NPC298647
0.8924	High Similarity	NPC200726
0.8919	High Similarity	NPC19862
0.8919	High Similarity	NPC280717
0.8919	High Similarity	NPC235195
0.8919	High Similarity	NPC271607
0.8897	High Similarity	NPC132723
0.8897	High Similarity	NPC76032
0.8889	High Similarity	NPC249817
0.8868	High Similarity	NPC177362
0.8867	High Similarity	NPC96930
0.8867	High Similarity	NPC32017
0.8844	High Similarity	NPC472410
0.8828	High Similarity	NPC216940
0.8828	High Similarity	NPC475482
0.8828	High Similarity	NPC22676
0.8828	High Similarity	NPC198621
0.882	High Similarity	NPC295941
0.882	High Similarity	NPC469778
0.882	High Similarity	NPC469776
0.882	High Similarity	NPC135334
0.882	High Similarity	NPC469774
0.882	High Similarity	NPC469772
0.882	High Similarity	NPC32723
0.882	High Similarity	NPC469773
0.882	High Similarity	NPC469775
0.882	High Similarity	NPC469777
0.882	High Similarity	NPC100925
0.8819	High Similarity	NPC173569
0.8819	High Similarity	NPC477874
0.8812	High Similarity	NPC202428
0.8812	High Similarity	NPC266545
0.8811	High Similarity	NPC475346
0.8811	High Similarity	NPC475627
0.8811	High Similarity	NPC18982
0.8811	High Similarity	NPC475457
0.8808	High Similarity	NPC292206
0.8784	High Similarity	NPC252133
0.8758	High Similarity	NPC472803
0.8725	High Similarity	NPC26045
0.8716	High Similarity	NPC35212
0.8658	High Similarity	NPC310621
0.8658	High Similarity	NPC235557
0.8649	High Similarity	NPC78987
0.8649	High Similarity	NPC82336
0.8649	High Similarity	NPC473612
0.8645	High Similarity	NPC62051
0.8621	High Similarity	NPC471110
0.86	High Similarity	NPC471876
0.86	High Similarity	NPC209085
0.86	High Similarity	NPC224884
0.8523	High Similarity	NPC172311
0.8523	High Similarity	NPC472801
0.8523	High Similarity	NPC29599
0.8516	High Similarity	NPC124842
0.8514	High Similarity	NPC234548
0.8514	High Similarity	NPC248287
0.8506	High Similarity	NPC327962
0.8506	High Similarity	NPC237441
0.8491	Intermediate Similarity	NPC185617
0.8456	Intermediate Similarity	NPC106055
0.8456	Intermediate Similarity	NPC110699
0.8456	Intermediate Similarity	NPC470616
0.8456	Intermediate Similarity	NPC470617
0.8438	Intermediate Similarity	NPC266365
0.8435	Intermediate Similarity	NPC252343
0.8425	Intermediate Similarity	NPC476282
0.8425	Intermediate Similarity	NPC475468
0.8411	Intermediate Similarity	NPC169214
0.8411	Intermediate Similarity	NPC229218
0.8411	Intermediate Similarity	NPC192597
0.8411	Intermediate Similarity	NPC141817
0.8411	Intermediate Similarity	NPC176030
0.8408	Intermediate Similarity	NPC305710
0.8403	Intermediate Similarity	NPC86257
0.84	Intermediate Similarity	NPC470035
0.8389	Intermediate Similarity	NPC139243
0.8389	Intermediate Similarity	NPC116742
0.8378	Intermediate Similarity	NPC120852
0.8378	Intermediate Similarity	NPC90431
0.8377	Intermediate Similarity	NPC477483
0.8377	Intermediate Similarity	NPC325032
0.8356	Intermediate Similarity	NPC239302
0.8333	Intermediate Similarity	NPC471875
0.8333	Intermediate Similarity	NPC475718
0.8333	Intermediate Similarity	NPC100420
0.8311	Intermediate Similarity	NPC103082
0.8311	Intermediate Similarity	NPC113295
0.8301	Intermediate Similarity	NPC309169
0.8301	Intermediate Similarity	NPC196941
0.8299	Intermediate Similarity	NPC327410
0.8289	Intermediate Similarity	NPC184935
0.8288	Intermediate Similarity	NPC243305
0.8276	Intermediate Similarity	NPC304622
0.8269	Intermediate Similarity	NPC261322
0.8264	Intermediate Similarity	NPC123228
0.8264	Intermediate Similarity	NPC123722
0.8264	Intermediate Similarity	NPC151167
0.8264	Intermediate Similarity	NPC276466
0.8264	Intermediate Similarity	NPC5018
0.8258	Intermediate Similarity	NPC52692
0.8258	Intermediate Similarity	NPC470757
0.825	Intermediate Similarity	NPC268602
0.8243	Intermediate Similarity	NPC11266
0.8243	Intermediate Similarity	NPC68779
0.8243	Intermediate Similarity	NPC4982
0.8243	Intermediate Similarity	NPC5310
0.8243	Intermediate Similarity	NPC176814
0.8243	Intermediate Similarity	NPC300776
0.8239	Intermediate Similarity	NPC472807
0.8239	Intermediate Similarity	NPC131532
0.8221	Intermediate Similarity	NPC25889
0.8219	Intermediate Similarity	NPC215941
0.8219	Intermediate Similarity	NPC65935
0.8219	Intermediate Similarity	NPC275724
0.8219	Intermediate Similarity	NPC123196
0.8219	Intermediate Similarity	NPC311419
0.8219	Intermediate Similarity	NPC137427
0.8219	Intermediate Similarity	NPC244246
0.8219	Intermediate Similarity	NPC319282
0.8219	Intermediate Similarity	NPC172673
0.8217	Intermediate Similarity	NPC178048
0.8212	Intermediate Similarity	NPC322021
0.821	Intermediate Similarity	NPC216916
0.8207	Intermediate Similarity	NPC278308
0.8205	Intermediate Similarity	NPC474556
0.8205	Intermediate Similarity	NPC264229
0.8205	Intermediate Similarity	NPC279442
0.8205	Intermediate Similarity	NPC46549
0.8194	Intermediate Similarity	NPC84076
0.8194	Intermediate Similarity	NPC472938
0.8194	Intermediate Similarity	NPC39361
0.8194	Intermediate Similarity	NPC472937
0.8194	Intermediate Similarity	NPC58752
0.8194	Intermediate Similarity	NPC90128
0.8194	Intermediate Similarity	NPC190849
0.8194	Intermediate Similarity	NPC179777
0.8194	Intermediate Similarity	NPC303680
0.8194	Intermediate Similarity	NPC472936
0.8194	Intermediate Similarity	NPC276014
0.8194	Intermediate Similarity	NPC171007
0.8188	Intermediate Similarity	NPC472804
0.8182	Intermediate Similarity	NPC312404
0.8182	Intermediate Similarity	NPC286809
0.8182	Intermediate Similarity	NPC300603
0.8182	Intermediate Similarity	NPC91694
0.8182	Intermediate Similarity	NPC273686
0.8182	Intermediate Similarity	NPC469683
0.8165	Intermediate Similarity	NPC472838
0.8165	Intermediate Similarity	NPC306011
0.816	Intermediate Similarity	NPC149389
0.816	Intermediate Similarity	NPC140346
0.8158	Intermediate Similarity	NPC100675
0.8155	Intermediate Similarity	NPC473630
0.8151	Intermediate Similarity	NPC83062
0.8146	Intermediate Similarity	NPC284409
0.8141	Intermediate Similarity	NPC1580
0.8138	Intermediate Similarity	NPC20404
0.8138	Intermediate Similarity	NPC12022
0.8138	Intermediate Similarity	NPC293641
0.8138	Intermediate Similarity	NPC20287
0.8137	Intermediate Similarity	NPC471878
0.8133	Intermediate Similarity	NPC471870
0.8129	Intermediate Similarity	NPC470038
0.8129	Intermediate Similarity	NPC75295
0.8129	Intermediate Similarity	NPC258856
0.8125	Intermediate Similarity	NPC257589
0.8125	Intermediate Similarity	NPC53305
0.8125	Intermediate Similarity	NPC280767
0.8125	Intermediate Similarity	NPC137416
0.8121	Intermediate Similarity	NPC37065
0.8121	Intermediate Similarity	NPC263212

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 NPC475454 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	899
0.2-0.3	1582
0.3-0.4	2561
0.4-0.5	2110
0.5-0.6	1144
0.6-0.7	488
0.7-0.8	57
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9236	High Similarity	NPD8166	Discontinued
0.8438	Intermediate Similarity	NPD8127	Discontinued
0.8269	Intermediate Similarity	NPD7458	Discontinued
0.8105	Intermediate Similarity	NPD7003	Approved
0.8081	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD3620	Phase 2
0.7962	Intermediate Similarity	NPD6273	Approved
0.7907	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7028	Phase 2
0.7871	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD4110	Phase 3
0.7862	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7228	Approved
0.7778	Intermediate Similarity	NPD37	Approved
0.7758	Intermediate Similarity	NPD6234	Discontinued
0.7756	Intermediate Similarity	NPD4628	Phase 3
0.7682	Intermediate Similarity	NPD8032	Phase 2
0.7636	Intermediate Similarity	NPD4965	Approved
0.7636	Intermediate Similarity	NPD4967	Phase 2
0.7636	Intermediate Similarity	NPD4966	Approved
0.7602	Intermediate Similarity	NPD5844	Phase 1
0.7588	Intermediate Similarity	NPD7473	Discontinued
0.7586	Intermediate Similarity	NPD8313	Approved
0.7586	Intermediate Similarity	NPD8312	Approved
0.7582	Intermediate Similarity	NPD6355	Discontinued
0.7566	Intermediate Similarity	NPD6663	Approved
0.755	Intermediate Similarity	NPD7095	Approved
0.7533	Intermediate Similarity	NPD5736	Approved
0.7532	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4060	Phase 1
0.7516	Intermediate Similarity	NPD4140	Approved
0.7514	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6798	Discontinued
0.7486	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7097	Phase 1
0.745	Intermediate Similarity	NPD1283	Approved
0.7427	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6166	Phase 2
0.7427	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD9494	Approved
0.7412	Intermediate Similarity	NPD6232	Discontinued
0.7389	Intermediate Similarity	NPD2935	Discontinued
0.7379	Intermediate Similarity	NPD5536	Phase 2
0.7375	Intermediate Similarity	NPD6190	Approved
0.7371	Intermediate Similarity	NPD7685	Pre-registration
0.7371	Intermediate Similarity	NPD7240	Approved
0.7356	Intermediate Similarity	NPD7074	Phase 3
0.7349	Intermediate Similarity	NPD1934	Approved
0.7347	Intermediate Similarity	NPD3019	Approved
0.7347	Intermediate Similarity	NPD4626	Approved
0.7347	Intermediate Similarity	NPD2932	Approved
0.7346	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7266	Discontinued
0.732	Intermediate Similarity	NPD3027	Phase 3
0.7305	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD8455	Phase 2
0.7299	Intermediate Similarity	NPD7054	Approved
0.7293	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6873	Phase 2
0.7289	Intermediate Similarity	NPD6677	Suspended
0.7278	Intermediate Similarity	NPD2438	Suspended
0.7263	Intermediate Similarity	NPD8434	Phase 2
0.7257	Intermediate Similarity	NPD7472	Approved
0.7251	Intermediate Similarity	NPD7199	Phase 2
0.725	Intermediate Similarity	NPD6674	Discontinued
0.725	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1281	Approved
0.7244	Intermediate Similarity	NPD5735	Approved
0.7233	Intermediate Similarity	NPD5763	Approved
0.7233	Intermediate Similarity	NPD5762	Approved
0.7226	Intermediate Similarity	NPD6233	Phase 2
0.7222	Intermediate Similarity	NPD5283	Phase 1
0.7219	Intermediate Similarity	NPD7768	Phase 2
0.7215	Intermediate Similarity	NPD2799	Discontinued
0.7205	Intermediate Similarity	NPD3750	Approved
0.7203	Intermediate Similarity	NPD228	Approved
0.7202	Intermediate Similarity	NPD7819	Suspended
0.7179	Intermediate Similarity	NPD2979	Phase 3
0.7176	Intermediate Similarity	NPD7075	Discontinued
0.7171	Intermediate Similarity	NPD2797	Approved
0.7167	Intermediate Similarity	NPD8150	Discontinued
0.7162	Intermediate Similarity	NPD1651	Approved
0.7162	Intermediate Similarity	NPD5691	Approved
0.7161	Intermediate Similarity	NPD3268	Approved
0.7152	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3818	Discontinued
0.7135	Intermediate Similarity	NPD7808	Phase 3
0.7134	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3657	Discovery
0.7134	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4380	Phase 2
0.7125	Intermediate Similarity	NPD2346	Discontinued
0.7118	Intermediate Similarity	NPD3882	Suspended
0.7117	Intermediate Similarity	NPD7236	Approved
0.7101	Intermediate Similarity	NPD1465	Phase 2
0.7101	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2801	Approved
0.709	Intermediate Similarity	NPD7680	Approved
0.7089	Intermediate Similarity	NPD6653	Approved
0.7086	Intermediate Similarity	NPD3972	Approved
0.7081	Intermediate Similarity	NPD4534	Discontinued
0.7079	Intermediate Similarity	NPD7251	Discontinued
0.7069	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD3455	Phase 2
0.7063	Intermediate Similarity	NPD6100	Approved
0.7063	Intermediate Similarity	NPD6099	Approved
0.7059	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3817	Phase 2
0.7059	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD2490	Approved
0.7049	Intermediate Similarity	NPD2488	Approved
0.7047	Intermediate Similarity	NPD1357	Approved
0.7039	Intermediate Similarity	NPD5327	Phase 3
0.7039	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD447	Suspended
0.7024	Intermediate Similarity	NPD6599	Discontinued
0.7022	Intermediate Similarity	NPD6797	Phase 2
0.702	Intermediate Similarity	NPD3092	Approved
0.7013	Intermediate Similarity	NPD2798	Approved
0.7013	Intermediate Similarity	NPD5647	Approved
0.7007	Intermediate Similarity	NPD7157	Approved
0.7006	Intermediate Similarity	NPD1653	Approved
0.7006	Intermediate Similarity	NPD4062	Phase 3
0.6994	Remote Similarity	NPD5494	Approved
0.6993	Remote Similarity	NPD8651	Approved
0.6987	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7008	Discontinued
0.698	Remote Similarity	NPD3091	Approved
0.6977	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7833	Phase 2
0.6977	Remote Similarity	NPD7831	Phase 2
0.6964	Remote Similarity	NPD3226	Approved
0.6962	Remote Similarity	NPD1613	Approved
0.6962	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2531	Phase 2
0.6957	Remote Similarity	NPD5405	Approved
0.6957	Remote Similarity	NPD5408	Approved
0.6957	Remote Similarity	NPD5404	Approved
0.6957	Remote Similarity	NPD5406	Approved
0.6954	Remote Similarity	NPD3026	Approved
0.6954	Remote Similarity	NPD3023	Approved
0.6954	Remote Similarity	NPD6959	Discontinued
0.6949	Remote Similarity	NPD3751	Discontinued
0.6948	Remote Similarity	NPD3094	Phase 2
0.6944	Remote Similarity	NPD3022	Approved
0.6944	Remote Similarity	NPD3021	Approved
0.6943	Remote Similarity	NPD3764	Approved
0.6941	Remote Similarity	NPD6801	Discontinued
0.6939	Remote Similarity	NPD2629	Approved
0.6933	Remote Similarity	NPD5585	Approved
0.6933	Remote Similarity	NPD3025	Approved
0.6933	Remote Similarity	NPD3024	Approved
0.6932	Remote Similarity	NPD2489	Approved
0.6932	Remote Similarity	NPD27	Approved
0.6928	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD230	Phase 1
0.691	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD8151	Discontinued
0.6905	Remote Similarity	NPD7239	Suspended
0.6903	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4624	Approved
0.6894	Remote Similarity	NPD3748	Approved
0.6889	Remote Similarity	NPD6559	Discontinued
0.6889	Remote Similarity	NPD7039	Approved
0.6889	Remote Similarity	NPD7038	Approved
0.6887	Remote Similarity	NPD1778	Approved
0.6883	Remote Similarity	NPD1876	Approved
0.6882	Remote Similarity	NPD7411	Suspended
0.6879	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6353	Approved
0.6871	Remote Similarity	NPD5958	Discontinued
0.6871	Remote Similarity	NPD1241	Discontinued
0.6871	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1511	Approved
0.6863	Remote Similarity	NPD1608	Approved
0.686	Remote Similarity	NPD5402	Approved
0.6852	Remote Similarity	NPD4476	Approved
0.6852	Remote Similarity	NPD4477	Approved
0.6848	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5403	Approved
0.6842	Remote Similarity	NPD3496	Discontinued
0.6842	Remote Similarity	NPD3847	Discontinued
0.6839	Remote Similarity	NPD3266	Approved
0.6839	Remote Similarity	NPD3267	Approved
0.6836	Remote Similarity	NPD2898	Approved
0.6835	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2313	Discontinued
0.6835	Remote Similarity	NPD7985	Registered
0.6823	Remote Similarity	NPD7435	Discontinued
0.6823	Remote Similarity	NPD7497	Discontinued
0.6818	Remote Similarity	NPD3787	Discontinued

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