NPASS Compound

Structure

NPC470601 OpenBabel07101719142D 80 88 0 0 1 0 0 0 0 0999 V2000 10.9435 -3.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0134 -6.4697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.4356 -7.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0710 -9.3424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2620 -8.7546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.2801 -5.1668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6045 -6.9146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -7.0431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.8544 -5.5826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8095 -5.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1723 -7.7569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6756 -5.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9155 -7.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7801 -2.8145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5827 -9.1115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7582 -2.6066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6691 -9.5183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -7.0431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.8763 -5.3747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0000 -7.0431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8981 -5.1668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 -9.6411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.9055 -2.9373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -8.7751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.1708 -4.3042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1756 -8.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -7.0431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.8326 -5.7905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8095 -4.3090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.2213 -7.4479 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 13.4846 -7.3968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6756 -6.8090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.0000 -8.7751 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 15.2364 -3.6805 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 12.6756 -3.8090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.4781 -8.1170 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.8666 -7.3968 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.0000 -8.7751 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 14.2582 -3.4726 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.5000 -7.9091 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 15.5454 -4.6315 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.0000 -8.7751 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 17.1927 -4.0963 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5000 -7.9091 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.5000 -9.6411 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 16.8837 -3.1453 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 18.4799 -5.2553 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0000 -7.0431 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 17.8107 -5.9984 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 12.1756 -8.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5891 -4.2157 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.5000 -7.9091 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.5000 -7.9091 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 16.5236 -4.8395 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.5000 -7.9091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -9.5072 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 2.0000 -10.5072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -11.5072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 18.1948 -1.1420 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 16.9348 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.2927 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 20.8703 -5.3892 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 20.7963 -3.9769 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 19.3840 -4.0509 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -5.1770 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 0.5000 -6.1770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -7.1770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 18.8900 -8.1355 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 20.0760 -7.3653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 19.3058 -6.1792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -10.5072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 17.5528 -2.4021 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 19.4580 -5.4632 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -6.1770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 18.1197 -6.9495 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -10.5072 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 17.2438 -1.4511 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 20.1271 -4.7200 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -6.1770 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 19.0979 -7.1574 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 29 1 0 0 0 0 2 30 1 0 0 0 0 3 31 1 0 0 0 0 4 50 1 0 0 0 0 5 50 1 0 0 0 0 6 51 1 0 0 0 0 7 52 1 0 0 0 0 8 53 1 0 0 0 0 9 54 1 0 0 0 0 10 12 1 0 0 0 0 10 29 1 0 0 0 0 11 13 2 0 0 0 0 11 30 1 0 0 0 0 12 32 1 0 0 0 0 13 37 1 0 0 0 0 14 16 1 0 0 0 0 14 35 1 0 0 0 0 15 17 1 0 0 0 0 15 36 1 0 0 0 0 16 39 1 0 0 0 0 17 38 1 0 0 0 0 18 20 1 0 0 0 0 18 40 1 0 0 0 0 19 21 1 0 0 0 0 19 41 1 0 0 0 0 20 52 1 0 0 0 0 21 51 1 0 0 0 0 22 33 1 0 0 0 0 22 45 1 0 0 0 0 23 34 1 0 0 0 0 23 46 1 0 0 0 0 24 42 1 0 0 0 0 24 44 1 0 0 0 0 25 43 1 0 0 0 0 25 47 1 0 0 0 0 26 31 2 0 0 0 0 26 50 1 0 0 0 0 27 48 1 0 0 0 0 27 53 1 0 0 0 0 28 49 1 0 0 0 0 28 54 1 0 0 0 0 29 35 1 0 0 0 0 30 36 1 0 0 0 0 31 32 1 0 0 0 0 32 37 1 0 0 0 0 33 38 1 0 0 0 0 33 40 1 0 0 0 0 34 39 1 0 0 0 0 34 41 1 0 0 0 0 35 51 1 0 0 0 0 36 52 1 0 0 0 0 37 50 1 0 0 0 0 38 52 1 0 0 0 0 39 51 1 0 0 0 0 40 53 1 0 0 0 0 41 54 1 0 0 0 0 42 45 1 0 0 0 0 42 53 1 0 0 0 0 43 46 1 0 0 0 0 43 54 1 0 0 0 0 44 48 1 0 0 0 0 44 55 1 0 0 0 0 45 71 1 0 0 0 0 46 72 1 0 0 0 0 47 49 1 0 0 0 0 47 73 1 0 0 0 0 48 74 1 0 0 0 0 49 75 1 0 0 0 0 56 76 1 0 0 0 0 57 76 2 0 0 0 0 58 76 2 0 0 0 0 59 77 1 0 0 0 0 60 77 2 0 0 0 0 61 77 2 0 0 0 0 62 78 1 0 0 0 0 63 78 2 0 0 0 0 64 78 2 0 0 0 0 65 79 1 0 0 0 0 66 79 2 0 0 0 0 67 79 2 0 0 0 0 68 80 1 0 0 0 0 69 80 2 0 0 0 0 70 80 2 0 0 0 0 71 76 1 0 0 0 0 72 77 1 0 0 0 0 73 78 1 0 0 0 0 74 79 1 0 0 0 0 75 80 1 0 0 0 0 M CHG 5 56 -1 59 -1 62 -1 65 -1 68 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	1227.41
Volume:	1130.807
LogP:	5.823
LogD:	3.155
LogS:	-5.884
# Rotatable Bonds:	17
TPSA:	352.38
# H-Bond Aceptor:	21
# H-Bond Donor:	1
# Rings:	9
# Heavy Atoms:	26

MedChem Properties

QED Drug-Likeness Score:	0.086
Synthetic Accessibility Score:	7.622
Fsp3:	0.926
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.019
MDCK Permeability:	2.4465687602059916e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.142
20% Bioavailability (F20%):	0.292
30% Bioavailability (F30%):	0.246

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	93.7818832397461%
Volume Distribution (VD):	1.761
Pgp-substrate:	1.6696629524230957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.656
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.859
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.027

ADMET: Excretion

Clearance (CL):	1.809
Half-life (T1/2):	0.0

ADMET: Toxicity

hERG Blockers:	0.809
Human Hepatotoxicity (H-HT):	0.951
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.971
Rat Oral Acute Toxicity:	0.999
Maximum Recommended Daily Dose:	0.998
Skin Sensitization:	0.999
Carcinogencity:	0.658
Eye Corrosion:	0.989
Eye Irritation:	0.539
Respiratory Toxicity:	0.995

Download Data

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

Natural Product: NPC470601

Natural Product ID:	NPC470601
*Common Name:**	Manadosterol A
IUPAC Name:	pentasodium;[(2S,3S,5S,6S,8S,9S,10R,13R,14S,17R)-17-[(Z,2R)-4-[(1S,5R)-5-[(3R)-3-[(2S,3S,5S,6S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-2,3,6-trisulfonatooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]butyl]-2,2,4-trimethylcyclopent-3-en-1-yl]but-3-en-2-yl]-3-hydroxy-10,13-dimethyl-2-sulfonatooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-6-yl] sulfate
Synonyms:	Manadosterol A
Standard InCHIKey:	XDFYDGOBWUFTDP-MMCNXTPJSA-I
Standard InCHI:	InChI=1S/C54H88O21S5.5Na/c1-29(35-14-16-39-34-23-46(72-77(59,60)61)43-25-47(73-78(62,63)64)49(75-80(68,69)70)28-54(43,9)41(34)19-21-51(35,39)6)10-12-32-31(3)26-50(4,5)37(32)13-11-30(2)36-15-17-38-33-22-45(71-76(56,57)58)42-24-44(55)48(74-79(65,66)67)27-53(42,8)40(33)18-20-52(36,38)7;;;;;/h11,13,26,29-30,32-49,55H,10,12,14-25,27-28H2,1-9H3,(H,56,57,58)(H,59,60,61)(H,62,63,64)(H,65,66,67)(H,68,69,70);;;;;/q;5*+1/p-5/b13-11-;;;;;/t29-,30-,32+,33+,34+,35-,36-,37+,38+,39+,40+,41+,42-,43-,44+,45+,46+,47+,48+,49+,51-,52-,53-,54-;;;;;/m1...../s1
SMILES:	CC1=CC(C(C1CCC(C)C2CCC3C2(CCC4C3CC(C5C4(CC(C(C5)OS(=O)(=O)[O-])OS(=O)(=O)[O-])C)OS(=O)(=O)[O-])C)C=CC(C)C6CCC7C6(CCC8C7CC(C9C8(CC(C(C9)O)OS(=O)(=O)[O-])C)OS(=O)(=O)[O-])C)(C)C.[Na+].[Na+].[Na+].[Na+].[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2087612
PubChem CID:	66554195
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
NPO33465	lissodendryx fibrosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22873794]

☑ 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	1

Activity Type	# Activity
PROTEIN-PROTEIN INTERACTION	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT22197	PROTEIN-PROTEIN INTERACTION	Ubiquitin-conjugating enzyme E2 N/Ubiquitin-conjugating enzyme E2 variant 1	Homo sapiens	IC50	=	90.0	nM	PMID[492205]
NPT22197	PROTEIN-PROTEIN INTERACTION	Ubiquitin-conjugating enzyme E2 N/Ubiquitin-conjugating enzyme E2 variant 1	Homo sapiens	Ratio IC50	=	1000.0	n.a.	PMID[492205]

☑ 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 NPC470601 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	292
0.1-0.2	2238
0.2-0.3	9498
0.3-0.4	15791
0.4-0.5	6787
0.5-0.6	4595
0.6-0.7	2975
0.7-0.8	514
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9688	High Similarity	NPC470602
0.8211	Intermediate Similarity	NPC469878
0.8041	Intermediate Similarity	NPC477604
0.8021	Intermediate Similarity	NPC478102
0.8	Intermediate Similarity	NPC477599
0.798	Intermediate Similarity	NPC105495
0.7961	Intermediate Similarity	NPC477226
0.7961	Intermediate Similarity	NPC316604
0.7959	Intermediate Similarity	NPC186145
0.7959	Intermediate Similarity	NPC477600
0.7959	Intermediate Similarity	NPC474657
0.7917	Intermediate Similarity	NPC207013
0.7879	Intermediate Similarity	NPC475664
0.7857	Intermediate Similarity	NPC478094
0.7857	Intermediate Similarity	NPC237344
0.7843	Intermediate Similarity	NPC477605
0.78	Intermediate Similarity	NPC477606
0.78	Intermediate Similarity	NPC109744
0.7778	Intermediate Similarity	NPC475313
0.7732	Intermediate Similarity	NPC253402
0.7732	Intermediate Similarity	NPC159168
0.7732	Intermediate Similarity	NPC141941
0.7732	Intermediate Similarity	NPC477818
0.7732	Intermediate Similarity	NPC110778
0.7732	Intermediate Similarity	NPC193870
0.7723	Intermediate Similarity	NPC473956
0.7723	Intermediate Similarity	NPC475751
0.77	Intermediate Similarity	NPC133588
0.7679	Intermediate Similarity	NPC475312
0.7677	Intermediate Similarity	NPC71520
0.7677	Intermediate Similarity	NPC269058
0.7677	Intermediate Similarity	NPC24277
0.7653	Intermediate Similarity	NPC238992
0.7653	Intermediate Similarity	NPC475798
0.7653	Intermediate Similarity	NPC127606
0.7629	Intermediate Similarity	NPC47763
0.7629	Intermediate Similarity	NPC248886
0.7624	Intermediate Similarity	NPC187785
0.7624	Intermediate Similarity	NPC259875
0.7604	Intermediate Similarity	NPC13554
0.7604	Intermediate Similarity	NPC236237
0.7604	Intermediate Similarity	NPC322313
0.7604	Intermediate Similarity	NPC102253
0.7604	Intermediate Similarity	NPC236112
0.76	Intermediate Similarity	NPC470620
0.7593	Intermediate Similarity	NPC16573
0.7579	Intermediate Similarity	NPC244385
0.7579	Intermediate Similarity	NPC102708
0.7579	Intermediate Similarity	NPC6978
0.7579	Intermediate Similarity	NPC138621
0.7579	Intermediate Similarity	NPC167037
0.7551	Intermediate Similarity	NPC211135
0.7551	Intermediate Similarity	NPC85095
0.7551	Intermediate Similarity	NPC216420
0.7545	Intermediate Similarity	NPC181467
0.7526	Intermediate Similarity	NPC474531
0.7526	Intermediate Similarity	NPC473534
0.7525	Intermediate Similarity	NPC474668
0.7523	Intermediate Similarity	NPC165033
0.7523	Intermediate Similarity	NPC273879
0.75	Intermediate Similarity	NPC476691
0.75	Intermediate Similarity	NPC159036
0.75	Intermediate Similarity	NPC273410
0.75	Intermediate Similarity	NPC476692
0.75	Intermediate Similarity	NPC312553
0.75	Intermediate Similarity	NPC288694
0.75	Intermediate Similarity	NPC80530
0.75	Intermediate Similarity	NPC139724
0.75	Intermediate Similarity	NPC201273
0.75	Intermediate Similarity	NPC6605
0.75	Intermediate Similarity	NPC474132
0.75	Intermediate Similarity	NPC94462
0.75	Intermediate Similarity	NPC472463
0.7477	Intermediate Similarity	NPC246124
0.7477	Intermediate Similarity	NPC180183
0.7477	Intermediate Similarity	NPC7341
0.7477	Intermediate Similarity	NPC208358
0.7477	Intermediate Similarity	NPC473200
0.7477	Intermediate Similarity	NPC220427
0.7476	Intermediate Similarity	NPC97404
0.7476	Intermediate Similarity	NPC41554
0.7476	Intermediate Similarity	NPC275671
0.7475	Intermediate Similarity	NPC209802
0.7475	Intermediate Similarity	NPC124172
0.7475	Intermediate Similarity	NPC255882
0.7475	Intermediate Similarity	NPC474493
0.7474	Intermediate Similarity	NPC202540
0.7456	Intermediate Similarity	NPC476671
0.7455	Intermediate Similarity	NPC208594
0.7455	Intermediate Similarity	NPC208477
0.7455	Intermediate Similarity	NPC127801
0.7455	Intermediate Similarity	NPC69737
0.7455	Intermediate Similarity	NPC194842
0.7455	Intermediate Similarity	NPC160816
0.7455	Intermediate Similarity	NPC152584
0.7455	Intermediate Similarity	NPC269627
0.7449	Intermediate Similarity	NPC30166
0.7431	Intermediate Similarity	NPC155010
0.7431	Intermediate Similarity	NPC16520
0.7431	Intermediate Similarity	NPC114874
0.7431	Intermediate Similarity	NPC473020
0.7431	Intermediate Similarity	NPC213190
0.7431	Intermediate Similarity	NPC286969
0.7431	Intermediate Similarity	NPC8039
0.7431	Intermediate Similarity	NPC131479
0.7431	Intermediate Similarity	NPC211879
0.7431	Intermediate Similarity	NPC120123
0.7431	Intermediate Similarity	NPC189852
0.7431	Intermediate Similarity	NPC31907
0.7431	Intermediate Similarity	NPC245280
0.7431	Intermediate Similarity	NPC157659
0.7431	Intermediate Similarity	NPC472252
0.7423	Intermediate Similarity	NPC287749
0.7423	Intermediate Similarity	NPC475679
0.7407	Intermediate Similarity	NPC472023
0.7407	Intermediate Similarity	NPC47566
0.7407	Intermediate Similarity	NPC4831
0.7407	Intermediate Similarity	NPC88000
0.7407	Intermediate Similarity	NPC309425
0.7407	Intermediate Similarity	NPC155974
0.7407	Intermediate Similarity	NPC160734
0.7407	Intermediate Similarity	NPC129372
0.7396	Intermediate Similarity	NPC285761
0.7396	Intermediate Similarity	NPC300499
0.7387	Intermediate Similarity	NPC63368
0.7387	Intermediate Similarity	NPC14946
0.7387	Intermediate Similarity	NPC208650
0.7383	Intermediate Similarity	NPC280825
0.7383	Intermediate Similarity	NPC234287
0.7379	Intermediate Similarity	NPC80561
0.7379	Intermediate Similarity	NPC204188
0.7379	Intermediate Similarity	NPC11216
0.7379	Intermediate Similarity	NPC3345
0.7379	Intermediate Similarity	NPC329596
0.7379	Intermediate Similarity	NPC291484
0.7374	Intermediate Similarity	NPC113978
0.7368	Intermediate Similarity	NPC237460
0.7368	Intermediate Similarity	NPC477602
0.7368	Intermediate Similarity	NPC14112
0.7368	Intermediate Similarity	NPC86305
0.7368	Intermediate Similarity	NPC473916
0.7368	Intermediate Similarity	NPC477601
0.7364	Intermediate Similarity	NPC475365
0.7364	Intermediate Similarity	NPC312774
0.7358	Intermediate Similarity	NPC471903
0.7353	Intermediate Similarity	NPC470542
0.7353	Intermediate Similarity	NPC67872
0.7347	Intermediate Similarity	NPC242350
0.7345	Intermediate Similarity	NPC472717
0.7339	Intermediate Similarity	NPC136816
0.7327	Intermediate Similarity	NPC261266
0.7327	Intermediate Similarity	NPC121981
0.7321	Intermediate Similarity	NPC159005
0.7321	Intermediate Similarity	NPC6931
0.732	Intermediate Similarity	NPC116119
0.732	Intermediate Similarity	NPC80297
0.732	Intermediate Similarity	NPC472742
0.732	Intermediate Similarity	NPC475727
0.7315	Intermediate Similarity	NPC473790
0.7315	Intermediate Similarity	NPC476195
0.7308	Intermediate Similarity	NPC210268
0.7304	Intermediate Similarity	NPC476693
0.7292	Intermediate Similarity	NPC157996
0.7292	Intermediate Similarity	NPC34177
0.7292	Intermediate Similarity	NPC40394
0.7292	Intermediate Similarity	NPC130136
0.7292	Intermediate Similarity	NPC101475
0.729	Intermediate Similarity	NPC474994
0.729	Intermediate Similarity	NPC476021
0.729	Intermediate Similarity	NPC476893
0.729	Intermediate Similarity	NPC476040
0.7282	Intermediate Similarity	NPC101886
0.7282	Intermediate Similarity	NPC470361
0.7281	Intermediate Similarity	NPC65167
0.7281	Intermediate Similarity	NPC472715
0.7273	Intermediate Similarity	NPC1272
0.7273	Intermediate Similarity	NPC296701
0.7273	Intermediate Similarity	NPC470614
0.7273	Intermediate Similarity	NPC473198
0.7273	Intermediate Similarity	NPC218616
0.7273	Intermediate Similarity	NPC7988
0.7264	Intermediate Similarity	NPC476894
0.7263	Intermediate Similarity	NPC178383
0.7263	Intermediate Similarity	NPC103822
0.7263	Intermediate Similarity	NPC231256
0.7263	Intermediate Similarity	NPC104387
0.7263	Intermediate Similarity	NPC240235
0.7263	Intermediate Similarity	NPC212879
0.7257	Intermediate Similarity	NPC474573
0.7257	Intermediate Similarity	NPC51925
0.7257	Intermediate Similarity	NPC154085
0.7257	Intermediate Similarity	NPC43976
0.7257	Intermediate Similarity	NPC296761
0.7257	Intermediate Similarity	NPC125361
0.7248	Intermediate Similarity	NPC476132
0.7245	Intermediate Similarity	NPC71535
0.7245	Intermediate Similarity	NPC78545
0.7238	Intermediate Similarity	NPC291373
0.7238	Intermediate Similarity	NPC98193
0.7232	Intermediate Similarity	NPC190395

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 NPC470601 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	229
0.1-0.2	2283
0.2-0.3	4651
0.3-0.4	1408
0.4-0.5	296
0.5-0.6	239
0.6-0.7	43
0.7-0.8	1
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
0.7604	Intermediate Similarity	NPD7525	Registered
0.7143	Intermediate Similarity	NPD7645	Phase 2
0.6907	Remote Similarity	NPD7339	Approved
0.6907	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6933	Approved
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD8294	Approved
0.6613	Remote Similarity	NPD8033	Approved
0.6613	Remote Similarity	NPD8378	Approved
0.6613	Remote Similarity	NPD8380	Approved
0.6613	Remote Similarity	NPD8296	Approved
0.6613	Remote Similarity	NPD8335	Approved
0.6613	Remote Similarity	NPD8379	Approved
0.6604	Remote Similarity	NPD7524	Approved
0.6585	Remote Similarity	NPD7516	Approved
0.6571	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD8035	Phase 2
0.6514	Remote Similarity	NPD6079	Approved
0.6514	Remote Similarity	NPD8034	Phase 2
0.6514	Remote Similarity	NPD7515	Phase 2
0.6504	Remote Similarity	NPD7327	Approved
0.6504	Remote Similarity	NPD7328	Approved
0.6481	Remote Similarity	NPD5328	Approved
0.6476	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4786	Approved
0.6471	Remote Similarity	NPD6929	Approved
0.6465	Remote Similarity	NPD6924	Approved
0.6465	Remote Similarity	NPD6926	Approved
0.646	Remote Similarity	NPD7638	Approved
0.6449	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6932	Approved
0.6429	Remote Similarity	NPD7152	Approved
0.6429	Remote Similarity	NPD7151	Approved
0.6429	Remote Similarity	NPD7150	Approved
0.6408	Remote Similarity	NPD7509	Discontinued
0.6408	Remote Similarity	NPD6931	Approved
0.6408	Remote Similarity	NPD6930	Phase 2
0.6404	Remote Similarity	NPD7640	Approved
0.6404	Remote Similarity	NPD7639	Approved
0.6396	Remote Similarity	NPD7748	Approved
0.6392	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6695	Phase 3
0.6373	Remote Similarity	NPD7145	Approved
0.6372	Remote Similarity	NPD7902	Approved
0.6355	Remote Similarity	NPD3618	Phase 1
0.6333	Remote Similarity	NPD4634	Approved
0.6327	Remote Similarity	NPD7144	Approved
0.6327	Remote Similarity	NPD7143	Approved
0.6321	Remote Similarity	NPD3668	Phase 3
0.6306	Remote Similarity	NPD4202	Approved
0.63	Remote Similarity	NPD4784	Approved
0.63	Remote Similarity	NPD4785	Approved
0.6296	Remote Similarity	NPD7750	Discontinued
0.6286	Remote Similarity	NPD3667	Approved
0.6283	Remote Similarity	NPD5221	Approved
0.6283	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5222	Approved
0.6275	Remote Similarity	NPD5776	Phase 2
0.6275	Remote Similarity	NPD6925	Approved
0.6263	Remote Similarity	NPD4243	Approved
0.6261	Remote Similarity	NPD5286	Approved
0.6261	Remote Similarity	NPD5285	Approved
0.6261	Remote Similarity	NPD4696	Approved
0.625	Remote Similarity	NPD7514	Phase 3
0.625	Remote Similarity	NPD7332	Phase 2
0.623	Remote Similarity	NPD8297	Approved
0.6228	Remote Similarity	NPD5173	Approved
0.6228	Remote Similarity	NPD4755	Approved
0.6224	Remote Similarity	NPD6922	Approved
0.6224	Remote Similarity	NPD6923	Approved
0.622	Remote Similarity	NPD7503	Approved
0.6207	Remote Similarity	NPD5223	Approved
0.619	Remote Similarity	NPD6902	Approved
0.6179	Remote Similarity	NPD8133	Approved
0.6179	Remote Similarity	NPD4632	Approved
0.6174	Remote Similarity	NPD5290	Discontinued
0.6167	Remote Similarity	NPD7320	Approved
0.6161	Remote Similarity	NPD8171	Discontinued
0.6161	Remote Similarity	NPD6399	Phase 3
0.6154	Remote Similarity	NPD7507	Approved
0.6154	Remote Similarity	NPD5225	Approved
0.6154	Remote Similarity	NPD5226	Approved
0.6154	Remote Similarity	NPD6683	Phase 2
0.6154	Remote Similarity	NPD4633	Approved
0.6154	Remote Similarity	NPD5224	Approved
0.6154	Remote Similarity	NPD5211	Phase 2
0.614	Remote Similarity	NPD4697	Phase 3
0.6126	Remote Similarity	NPD7136	Phase 2
0.6124	Remote Similarity	NPD8328	Phase 3
0.6121	Remote Similarity	NPD4700	Approved
0.6116	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6893	Approved
0.6106	Remote Similarity	NPD7900	Approved
0.6106	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD4754	Approved
0.6102	Remote Similarity	NPD5175	Approved
0.6102	Remote Similarity	NPD5174	Approved
0.6095	Remote Similarity	NPD4748	Discontinued
0.6083	Remote Similarity	NPD6412	Phase 2
0.6061	Remote Similarity	NPD7736	Approved
0.6058	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.605	Remote Similarity	NPD5141	Approved
0.6038	Remote Similarity	NPD6898	Phase 1
0.6033	Remote Similarity	NPD4729	Approved
0.6033	Remote Similarity	NPD6881	Approved
0.6033	Remote Similarity	NPD4730	Approved
0.6033	Remote Similarity	NPD6899	Approved
0.6019	Remote Similarity	NPD3666	Approved
0.6019	Remote Similarity	NPD3665	Phase 1
0.6019	Remote Similarity	NPD3133	Approved
0.6016	Remote Similarity	NPD6650	Approved
0.6016	Remote Similarity	NPD8130	Phase 1
0.6016	Remote Similarity	NPD6319	Approved
0.6016	Remote Similarity	NPD6649	Approved
0.6016	Remote Similarity	NPD6054	Approved
0.6015	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD4195	Approved
0.6	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD4767	Approved
0.5985	Remote Similarity	NPD7078	Approved
0.5984	Remote Similarity	NPD6372	Approved
0.5984	Remote Similarity	NPD6373	Approved
0.5968	Remote Similarity	NPD6882	Approved
0.595	Remote Similarity	NPD5697	Approved
0.5943	Remote Similarity	NPD6928	Phase 2
0.5935	Remote Similarity	NPD5249	Phase 3
0.5935	Remote Similarity	NPD5247	Approved
0.5935	Remote Similarity	NPD7290	Approved
0.5935	Remote Similarity	NPD5251	Approved
0.5935	Remote Similarity	NPD5248	Approved
0.5935	Remote Similarity	NPD7102	Approved
0.5935	Remote Similarity	NPD5250	Approved
0.5935	Remote Similarity	NPD6883	Approved
0.5935	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD5135	Approved
0.5929	Remote Similarity	NPD7087	Discontinued
0.5923	Remote Similarity	NPD6370	Approved
0.5922	Remote Similarity	NPD4190	Phase 3
0.5922	Remote Similarity	NPD8264	Approved
0.5922	Remote Similarity	NPD5275	Approved
0.5906	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD6009	Approved
0.5906	Remote Similarity	NPD7115	Discovery
0.5905	Remote Similarity	NPD6697	Approved
0.5905	Remote Similarity	NPD6118	Approved
0.5905	Remote Similarity	NPD6115	Approved
0.5905	Remote Similarity	NPD6114	Approved
0.5902	Remote Similarity	NPD6011	Approved
0.5893	Remote Similarity	NPD4753	Phase 2
0.5891	Remote Similarity	NPD6059	Approved
0.5887	Remote Similarity	NPD6847	Approved
0.5887	Remote Similarity	NPD6617	Approved
0.5887	Remote Similarity	NPD6869	Approved
0.5887	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7632	Discontinued
0.5854	Remote Similarity	NPD6014	Approved
0.5854	Remote Similarity	NPD6013	Approved
0.5854	Remote Similarity	NPD6012	Approved
0.5846	Remote Similarity	NPD6015	Approved
0.5846	Remote Similarity	NPD6016	Approved
0.5839	Remote Similarity	NPD8450	Suspended
0.5833	Remote Similarity	NPD7492	Approved
0.582	Remote Similarity	NPD5701	Approved
0.581	Remote Similarity	NPD6116	Phase 1
0.5806	Remote Similarity	NPD5169	Approved
0.5802	Remote Similarity	NPD5988	Approved
0.5793	Remote Similarity	NPD7625	Phase 1
0.5789	Remote Similarity	NPD6616	Approved
0.5789	Remote Similarity	NPD7637	Suspended
0.578	Remote Similarity	NPD4788	Approved
0.5776	Remote Similarity	NPD5210	Approved
0.5776	Remote Similarity	NPD4629	Approved
0.5772	Remote Similarity	NPD5168	Approved
0.5772	Remote Similarity	NPD5128	Approved
0.5766	Remote Similarity	NPD8449	Approved
0.5766	Remote Similarity	NPD5279	Phase 3
0.576	Remote Similarity	NPD5217	Approved
0.576	Remote Similarity	NPD5216	Approved
0.576	Remote Similarity	NPD5215	Approved
0.576	Remote Similarity	NPD5127	Approved
0.5758	Remote Similarity	NPD7604	Phase 2
0.5758	Remote Similarity	NPD6067	Discontinued
0.5746	Remote Similarity	NPD8293	Discontinued
0.5738	Remote Similarity	NPD6008	Approved
0.5725	Remote Similarity	NPD5983	Phase 2
0.5714	Remote Similarity	NPD6117	Approved
0.5702	Remote Similarity	NPD6700	Approved
0.5702	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD4223	Phase 3
0.5688	Remote Similarity	NPD4221	Approved
0.5686	Remote Similarity	NPD4787	Phase 1
0.5678	Remote Similarity	NPD6084	Phase 2
0.5678	Remote Similarity	NPD6083	Phase 2
0.5676	Remote Similarity	NPD5329	Approved
0.5672	Remote Similarity	NPD6336	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