NPASS Compound

Structure

NPC29447 OpenBabel07101718242D 31 34 0 0 1 0 0 0 0 0999 V2000 2.4248 4.9196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8246 5.4395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8244 3.0718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1743 1.4260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5238 -0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2242 3.5918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0760 2.6679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6826 -2.9143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8413 -2.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4949 -0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9239 -1.2716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2064 -1.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6826 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3651 -0.9714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8413 0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3651 -2.9143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4746 4.7176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1744 3.7938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2241 1.2241 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5238 -2.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2064 -2.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8413 -1.4571 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9239 0.3002 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6826 -0.9714 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9714 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3951 0.8874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5238 -1.4571 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 -5.0477 -2.9143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1759 1.6733 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3612 0.9890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 2 0 0 0 0 6 7 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 25 1 0 0 0 0 12 14 2 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 19 4 1 1 0 0 0 19 23 1 0 0 0 0 20 27 1 0 0 0 0 21 29 2 0 0 0 0 22 9 1 6 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 28 1 1 0 0 0 24 27 1 1 0 0 0 25 28 1 1 0 0 0 26 30 2 0 0 0 0 26 31 1 0 0 0 0 27 5 1 1 0 0 0 28 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.3
Volume:	471.807
LogP:	6.375
LogD:	5.208
LogS:	-4.956
# Rotatable Bonds:	6
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.488
Synthetic Accessibility Score:	4.769
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.063
MDCK Permeability:	1.9074439478572458e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.49
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.186
Plasma Protein Binding (PPB):	92.90884399414062%
Volume Distribution (VD):	0.599
Pgp-substrate:	3.219088077545166%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.254
CYP2C19-inhibitor:	0.072
CYP2C19-substrate:	0.632
CYP2C9-inhibitor:	0.43
CYP2C9-substrate:	0.52
CYP2D6-inhibitor:	0.101
CYP2D6-substrate:	0.039
CYP3A4-inhibitor:	0.857
CYP3A4-substrate:	0.639

ADMET: Excretion

Clearance (CL):	2.406
Half-life (T1/2):	0.201

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.481
Drug-inuced Liver Injury (DILI):	0.366
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.29
Maximum Recommended Daily Dose:	0.765
Skin Sensitization:	0.951
Carcinogencity:	0.826
Eye Corrosion:	0.871
Eye Irritation:	0.15
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC29447

Natural Product ID:	NPC29447
*Common Name:**	Norselic Aci C
IUPAC Name:	(8R,9S,10R,13S,14S,17R)-10-methyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-13-carboxylic acid
Synonyms:	Norselic Acid C
Standard InCHIKey:	JHPMFVKZPIBTMK-PBWAOFFKSA-N
Standard InCHI:	InChI=1S/C28H40O3/c1-17(2)18(3)6-7-19(4)23-10-11-25-22-9-8-20-16-21(29)12-14-27(20,5)24(22)13-15-28(23,25)26(30)31/h12,14,16-17,19,22-25H,3,6-11,13,15H2,1-2,4-5H3,(H,30,31)/t19-,22-,23-,24+,25+,27+,28+/m1/s1
SMILES:	C=C(C(C)C)CC[C@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1221625
PubChem CID:	44557718
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

*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
NPO33060	crella sp.	Species	Crellidae	Eukaryota	n.a.	Antarctic	n.a.	PMID[19848433]

☑ 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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	2.6	uM	PMID[529437]

☑ 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 NPC29447 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	162
0.1-0.2	1008
0.2-0.3	5551
0.3-0.4	14939
0.4-0.5	7501
0.5-0.6	6910
0.6-0.7	4364
0.7-0.8	1869
0.8-0.85	279
0.85-0.9	102
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.962	High Similarity	NPC320514
0.9518	High Similarity	NPC262043
0.9494	High Similarity	NPC147066
0.9494	High Similarity	NPC477372
0.9277	High Similarity	NPC136948
0.925	High Similarity	NPC278459
0.925	High Similarity	NPC201912
0.925	High Similarity	NPC38350
0.9241	High Similarity	NPC477371
0.9136	High Similarity	NPC260956
0.9136	High Similarity	NPC100297
0.907	High Similarity	NPC204341
0.9048	High Similarity	NPC93778
0.9036	High Similarity	NPC474537
0.9024	High Similarity	NPC83569
0.9024	High Similarity	NPC168188
0.9024	High Similarity	NPC470015
0.9024	High Similarity	NPC69279
0.9012	High Similarity	NPC471898
0.8987	High Similarity	NPC165711
0.8916	High Similarity	NPC164577
0.8916	High Similarity	NPC214043
0.8916	High Similarity	NPC85774
0.8902	High Similarity	NPC238991
0.8902	High Similarity	NPC472239
0.8902	High Similarity	NPC193347
0.8902	High Similarity	NPC133391
0.8902	High Similarity	NPC302661
0.8824	High Similarity	NPC58063
0.8824	High Similarity	NPC96496
0.8824	High Similarity	NPC236618
0.881	High Similarity	NPC94531
0.881	High Similarity	NPC469948
0.881	High Similarity	NPC311702
0.881	High Similarity	NPC123319
0.8795	High Similarity	NPC167103
0.8795	High Similarity	NPC477373
0.8795	High Similarity	NPC97913
0.8795	High Similarity	NPC477852
0.8778	High Similarity	NPC108078
0.8765	High Similarity	NPC215843
0.8765	High Similarity	NPC158846
0.8764	High Similarity	NPC171395
0.875	High Similarity	NPC471035
0.875	High Similarity	NPC212661
0.8734	High Similarity	NPC279666
0.8734	High Similarity	NPC192540
0.8721	High Similarity	NPC117122
0.8706	High Similarity	NPC155011
0.8706	High Similarity	NPC145879
0.8706	High Similarity	NPC186975
0.8706	High Similarity	NPC474778
0.8706	High Similarity	NPC474733
0.8706	High Similarity	NPC472869
0.8706	High Similarity	NPC31564
0.8706	High Similarity	NPC474732
0.869	High Similarity	NPC144258
0.869	High Similarity	NPC473246
0.869	High Similarity	NPC472864
0.869	High Similarity	NPC237712
0.869	High Similarity	NPC96095
0.869	High Similarity	NPC19849
0.869	High Similarity	NPC472865
0.8675	High Similarity	NPC142253
0.8675	High Similarity	NPC472867
0.8675	High Similarity	NPC3511
0.8659	High Similarity	NPC472478
0.8659	High Similarity	NPC476809
0.8642	High Similarity	NPC74410
0.8636	High Similarity	NPC473986
0.8636	High Similarity	NPC272746
0.8636	High Similarity	NPC474018
0.8636	High Similarity	NPC218301
0.8625	High Similarity	NPC180886
0.8625	High Similarity	NPC69143
0.8621	High Similarity	NPC474570
0.8621	High Similarity	NPC66344
0.8608	High Similarity	NPC183503
0.8608	High Similarity	NPC161923
0.8608	High Similarity	NPC241854
0.8608	High Similarity	NPC283908
0.8608	High Similarity	NPC103958
0.8608	High Similarity	NPC476046
0.8608	High Similarity	NPC251970
0.8605	High Similarity	NPC142361
0.8605	High Similarity	NPC475740
0.8605	High Similarity	NPC474684
0.8588	High Similarity	NPC269638
0.8588	High Similarity	NPC473038
0.8588	High Similarity	NPC11711
0.8588	High Similarity	NPC142649
0.8571	High Similarity	NPC102197
0.8571	High Similarity	NPC105803
0.8571	High Similarity	NPC472740
0.8556	High Similarity	NPC476174
0.8554	High Similarity	NPC162632
0.8554	High Similarity	NPC263272
0.8554	High Similarity	NPC274050
0.8554	High Similarity	NPC267691
0.8539	High Similarity	NPC474807
0.8539	High Similarity	NPC474736
0.8537	High Similarity	NPC192744
0.8537	High Similarity	NPC231431
0.8519	High Similarity	NPC66105
0.8519	High Similarity	NPC472300
0.8519	High Similarity	NPC97377
0.8519	High Similarity	NPC107039
0.8519	High Similarity	NPC471897
0.8519	High Similarity	NPC471899
0.8506	High Similarity	NPC472870
0.8488	Intermediate Similarity	NPC222613
0.8488	Intermediate Similarity	NPC475022
0.8488	Intermediate Similarity	NPC195640
0.8488	Intermediate Similarity	NPC118648
0.8488	Intermediate Similarity	NPC6247
0.8481	Intermediate Similarity	NPC474228
0.8481	Intermediate Similarity	NPC303613
0.8481	Intermediate Similarity	NPC251705
0.8478	Intermediate Similarity	NPC114274
0.8471	Intermediate Similarity	NPC221758
0.8471	Intermediate Similarity	NPC472265
0.8471	Intermediate Similarity	NPC33913
0.8471	Intermediate Similarity	NPC329043
0.8471	Intermediate Similarity	NPC87552
0.8471	Intermediate Similarity	NPC321187
0.8471	Intermediate Similarity	NPC165064
0.8471	Intermediate Similarity	NPC178025
0.8471	Intermediate Similarity	NPC181743
0.8471	Intermediate Similarity	NPC82902
0.8471	Intermediate Similarity	NPC161423
0.8471	Intermediate Similarity	NPC248758
0.8471	Intermediate Similarity	NPC227064
0.8471	Intermediate Similarity	NPC209882
0.8471	Intermediate Similarity	NPC59453
0.8471	Intermediate Similarity	NPC16287
0.8471	Intermediate Similarity	NPC58841
0.8462	Intermediate Similarity	NPC472941
0.8462	Intermediate Similarity	NPC456
0.8462	Intermediate Similarity	NPC29152
0.8452	Intermediate Similarity	NPC327969
0.8452	Intermediate Similarity	NPC251779
0.8452	Intermediate Similarity	NPC321289
0.8452	Intermediate Similarity	NPC69101
0.8434	Intermediate Similarity	NPC26139
0.8434	Intermediate Similarity	NPC2482
0.8434	Intermediate Similarity	NPC37038
0.8427	Intermediate Similarity	NPC475806
0.8427	Intermediate Similarity	NPC154101
0.8415	Intermediate Similarity	NPC260385
0.8415	Intermediate Similarity	NPC110094
0.8415	Intermediate Similarity	NPC82635
0.8415	Intermediate Similarity	NPC275494
0.8415	Intermediate Similarity	NPC280654
0.8415	Intermediate Similarity	NPC179028
0.8415	Intermediate Similarity	NPC471409
0.8409	Intermediate Similarity	NPC474704
0.8409	Intermediate Similarity	NPC477943
0.8409	Intermediate Similarity	NPC305039
0.8409	Intermediate Similarity	NPC268406
0.8409	Intermediate Similarity	NPC1015
0.8409	Intermediate Similarity	NPC31985
0.8409	Intermediate Similarity	NPC477973
0.8409	Intermediate Similarity	NPC26959
0.8409	Intermediate Similarity	NPC309603
0.8409	Intermediate Similarity	NPC475921
0.8409	Intermediate Similarity	NPC473999
0.8409	Intermediate Similarity	NPC186688
0.8395	Intermediate Similarity	NPC20466
0.8395	Intermediate Similarity	NPC69408
0.8395	Intermediate Similarity	NPC89294
0.8395	Intermediate Similarity	NPC246445
0.8391	Intermediate Similarity	NPC128644
0.8391	Intermediate Similarity	NPC159046
0.8391	Intermediate Similarity	NPC233836
0.8391	Intermediate Similarity	NPC476293
0.8391	Intermediate Similarity	NPC187376
0.8391	Intermediate Similarity	NPC476409
0.8391	Intermediate Similarity	NPC136548
0.8375	Intermediate Similarity	NPC309852
0.8372	Intermediate Similarity	NPC8571
0.8372	Intermediate Similarity	NPC474218
0.8372	Intermediate Similarity	NPC323765
0.8372	Intermediate Similarity	NPC470223
0.8372	Intermediate Similarity	NPC60350
0.8372	Intermediate Similarity	NPC471224
0.8372	Intermediate Similarity	NPC474680
0.8372	Intermediate Similarity	NPC470574
0.837	Intermediate Similarity	NPC156546
0.8354	Intermediate Similarity	NPC305501
0.8354	Intermediate Similarity	NPC115023
0.8354	Intermediate Similarity	NPC234707
0.8354	Intermediate Similarity	NPC54123
0.8354	Intermediate Similarity	NPC160817
0.8353	Intermediate Similarity	NPC70834
0.8353	Intermediate Similarity	NPC3856
0.8353	Intermediate Similarity	NPC279639
0.8353	Intermediate Similarity	NPC49019
0.8333	Intermediate Similarity	NPC142244
0.8333	Intermediate Similarity	NPC90055
0.8333	Intermediate Similarity	NPC473217

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 NPC29447 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1326
0.2-0.3	3953
0.3-0.4	2517
0.4-0.5	695
0.5-0.6	198
0.6-0.7	118
0.7-0.8	125
0.8-0.85	40
0.85-0.9	24
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8902	High Similarity	NPD4223	Phase 3
0.8902	High Similarity	NPD4221	Approved
0.881	High Similarity	NPD5329	Approved
0.8706	High Similarity	NPD5690	Phase 2
0.869	High Similarity	NPD4197	Approved
0.8636	High Similarity	NPD5281	Approved
0.8636	High Similarity	NPD6079	Approved
0.8636	High Similarity	NPD5284	Approved
0.8537	High Similarity	NPD4195	Approved
0.8506	High Similarity	NPD6672	Approved
0.8506	High Similarity	NPD5737	Approved
0.8488	Intermediate Similarity	NPD4693	Phase 3
0.8488	Intermediate Similarity	NPD6684	Approved
0.8488	Intermediate Similarity	NPD7521	Approved
0.8488	Intermediate Similarity	NPD4689	Approved
0.8488	Intermediate Similarity	NPD4690	Approved
0.8488	Intermediate Similarity	NPD7334	Approved
0.8488	Intermediate Similarity	NPD6409	Approved
0.8488	Intermediate Similarity	NPD5330	Approved
0.8488	Intermediate Similarity	NPD4688	Approved
0.8488	Intermediate Similarity	NPD4138	Approved
0.8488	Intermediate Similarity	NPD5205	Approved
0.8488	Intermediate Similarity	NPD7146	Approved
0.8471	Intermediate Similarity	NPD3666	Approved
0.8471	Intermediate Similarity	NPD3133	Approved
0.8471	Intermediate Similarity	NPD3665	Phase 1
0.8471	Intermediate Similarity	NPD4786	Approved
0.8415	Intermediate Similarity	NPD3617	Approved
0.8409	Intermediate Similarity	NPD6673	Approved
0.8409	Intermediate Similarity	NPD6904	Approved
0.8409	Intermediate Similarity	NPD5328	Approved
0.8409	Intermediate Similarity	NPD6080	Approved
0.837	Intermediate Similarity	NPD6083	Phase 2
0.837	Intermediate Similarity	NPD6084	Phase 2
0.8333	Intermediate Similarity	NPD6399	Phase 3
0.8295	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD5208	Approved
0.8295	Intermediate Similarity	NPD6903	Approved
0.8276	Intermediate Similarity	NPD5280	Approved
0.8276	Intermediate Similarity	NPD6098	Approved
0.8276	Intermediate Similarity	NPD4694	Approved
0.8276	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD3618	Phase 1
0.8235	Intermediate Similarity	NPD3667	Approved
0.8228	Intermediate Similarity	NPD4747	Approved
0.8228	Intermediate Similarity	NPD4691	Approved
0.8214	Intermediate Similarity	NPD4695	Discontinued
0.8202	Intermediate Similarity	NPD4753	Phase 2
0.8152	Intermediate Similarity	NPD4629	Approved
0.8152	Intermediate Similarity	NPD5695	Phase 3
0.8152	Intermediate Similarity	NPD5210	Approved
0.8148	Intermediate Similarity	NPD4058	Approved
0.8111	Intermediate Similarity	NPD5207	Approved
0.8101	Intermediate Similarity	NPD4137	Phase 3
0.8085	Intermediate Similarity	NPD5696	Approved
0.8068	Intermediate Similarity	NPD4519	Discontinued
0.8068	Intermediate Similarity	NPD5279	Phase 3
0.8068	Intermediate Similarity	NPD4623	Approved
0.8065	Intermediate Similarity	NPD5222	Approved
0.8065	Intermediate Similarity	NPD5221	Approved
0.8065	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD7515	Phase 2
0.8022	Intermediate Similarity	NPD5694	Approved
0.8022	Intermediate Similarity	NPD6050	Approved
0.8022	Intermediate Similarity	NPD5693	Phase 1
0.8	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.798	Intermediate Similarity	NPD6881	Approved
0.798	Intermediate Similarity	NPD6899	Approved
0.7979	Intermediate Similarity	NPD5173	Approved
0.7978	Intermediate Similarity	NPD3573	Approved
0.7957	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD4202	Approved
0.7931	Intermediate Similarity	NPD4788	Approved
0.7927	Intermediate Similarity	NPD4687	Approved
0.7927	Intermediate Similarity	NPD5733	Approved
0.7912	Intermediate Similarity	NPD5692	Phase 3
0.7879	Intermediate Similarity	NPD5697	Approved
0.7849	Intermediate Similarity	NPD7748	Approved
0.7849	Intermediate Similarity	NPD6001	Approved
0.7822	Intermediate Similarity	NPD7102	Approved
0.7822	Intermediate Similarity	NPD6883	Approved
0.7822	Intermediate Similarity	NPD7290	Approved
0.7812	Intermediate Similarity	NPD5285	Approved
0.7812	Intermediate Similarity	NPD5286	Approved
0.7812	Intermediate Similarity	NPD4696	Approved
0.7812	Intermediate Similarity	NPD6404	Discontinued
0.78	Intermediate Similarity	NPD6011	Approved
0.7778	Intermediate Similarity	NPD6675	Approved
0.7778	Intermediate Similarity	NPD6402	Approved
0.7778	Intermediate Similarity	NPD7128	Approved
0.7778	Intermediate Similarity	NPD5739	Approved
0.7753	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD6847	Approved
0.7745	Intermediate Similarity	NPD6649	Approved
0.7745	Intermediate Similarity	NPD8130	Phase 1
0.7745	Intermediate Similarity	NPD6650	Approved
0.7745	Intermediate Similarity	NPD6617	Approved
0.7745	Intermediate Similarity	NPD6869	Approved
0.7732	Intermediate Similarity	NPD5223	Approved
0.7723	Intermediate Similarity	NPD6012	Approved
0.7723	Intermediate Similarity	NPD6013	Approved
0.7723	Intermediate Similarity	NPD6014	Approved
0.7717	Intermediate Similarity	NPD4096	Approved
0.7711	Intermediate Similarity	NPD4784	Approved
0.7711	Intermediate Similarity	NPD4785	Approved
0.7701	Intermediate Similarity	NPD4692	Approved
0.7701	Intermediate Similarity	NPD4139	Approved
0.7692	Intermediate Similarity	NPD4518	Approved
0.7684	Intermediate Similarity	NPD4697	Phase 3
0.7684	Intermediate Similarity	NPD7614	Phase 1
0.7683	Intermediate Similarity	NPD4243	Approved
0.7683	Intermediate Similarity	NPD5276	Approved
0.767	Intermediate Similarity	NPD8297	Approved
0.767	Intermediate Similarity	NPD6882	Approved
0.7653	Intermediate Similarity	NPD5225	Approved
0.7653	Intermediate Similarity	NPD5091	Approved
0.7653	Intermediate Similarity	NPD5226	Approved
0.7653	Intermediate Similarity	NPD5224	Approved
0.7653	Intermediate Similarity	NPD5211	Phase 2
0.7653	Intermediate Similarity	NPD4633	Approved
0.764	Intermediate Similarity	NPD3668	Phase 3
0.7624	Intermediate Similarity	NPD7320	Approved
0.7604	Intermediate Similarity	NPD7902	Approved
0.7604	Intermediate Similarity	NPD4755	Approved
0.7576	Intermediate Similarity	NPD5175	Approved
0.7576	Intermediate Similarity	NPD5174	Approved
0.7553	Intermediate Similarity	NPD5133	Approved
0.7549	Intermediate Similarity	NPD6372	Approved
0.7549	Intermediate Similarity	NPD6373	Approved
0.7531	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD5701	Approved
0.7525	Intermediate Similarity	NPD6614	Approved
0.75	Intermediate Similarity	NPD5141	Approved
0.75	Intermediate Similarity	NPD4224	Phase 2
0.747	Intermediate Similarity	NPD6081	Approved
0.7453	Intermediate Similarity	NPD6868	Approved
0.7449	Intermediate Similarity	NPD4700	Approved
0.7429	Intermediate Similarity	NPD4632	Approved
0.7416	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7339	Approved
0.7412	Intermediate Similarity	NPD6942	Approved
0.7404	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6052	Approved
0.7396	Intermediate Similarity	NPD5654	Approved
0.7383	Intermediate Similarity	NPD7115	Discovery
0.7356	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7638	Approved
0.7315	Intermediate Similarity	NPD6335	Approved
0.7292	Intermediate Similarity	NPD7900	Approved
0.7292	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD4730	Approved
0.7282	Intermediate Similarity	NPD5168	Approved
0.7282	Intermediate Similarity	NPD4729	Approved
0.7273	Intermediate Similarity	NPD7640	Approved
0.7273	Intermediate Similarity	NPD7639	Approved
0.7263	Intermediate Similarity	NPD8034	Phase 2
0.7263	Intermediate Similarity	NPD8035	Phase 2
0.7248	Intermediate Similarity	NPD7100	Approved
0.7248	Intermediate Similarity	NPD7101	Approved
0.7245	Intermediate Similarity	NPD5959	Approved
0.7228	Intermediate Similarity	NPD4754	Approved
0.7222	Intermediate Similarity	NPD6009	Approved
0.7222	Intermediate Similarity	NPD6317	Approved
0.7209	Intermediate Similarity	NPD4190	Phase 3
0.7209	Intermediate Similarity	NPD5275	Approved
0.7184	Intermediate Similarity	NPD6412	Phase 2
0.7174	Intermediate Similarity	NPD1694	Approved
0.7156	Intermediate Similarity	NPD6313	Approved
0.7156	Intermediate Similarity	NPD6314	Approved
0.7143	Intermediate Similarity	NPD5169	Approved
0.7143	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5251	Approved
0.7143	Intermediate Similarity	NPD4634	Approved
0.7143	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5135	Approved
0.7143	Intermediate Similarity	NPD5248	Approved
0.7143	Intermediate Similarity	NPD7732	Phase 3
0.7143	Intermediate Similarity	NPD5249	Phase 3
0.7143	Intermediate Similarity	NPD5250	Approved
0.7143	Intermediate Similarity	NPD5247	Approved
0.713	Intermediate Similarity	NPD6274	Approved
0.7126	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5128	Approved
0.7108	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5360	Phase 3
0.7093	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6008	Approved
0.7087	Intermediate Similarity	NPD4768	Approved
0.7087	Intermediate Similarity	NPD4767	Approved
0.7075	Intermediate Similarity	NPD5215	Approved
0.7075	Intermediate Similarity	NPD5127	Approved
0.7075	Intermediate Similarity	NPD5217	Approved
0.7075	Intermediate Similarity	NPD5216	Approved
0.7073	Intermediate Similarity	NPD7331	Phase 2
0.7027	Intermediate Similarity	NPD6319	Approved
0.7	Intermediate Similarity	NPD7525	Registered
0.6991	Remote Similarity	NPD7604	Phase 2
0.6989	Remote Similarity	NPD5363	Approved
0.6979	Remote Similarity	NPD5785	Approved
0.6964	Remote Similarity	NPD5983	Phase 2

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