NPASS Compound

Structure

NPC204341 OpenBabel07101718292D 33 36 0 0 1 0 0 0 0 0999 V2000 2.3039 2.5474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7791 3.2790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4287 4.9274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1777 1.4283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3786 2.8481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4973 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9254 -1.2736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0761 2.6721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2131 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3705 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2246 3.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3705 -2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1280 4.0021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2260 1.2260 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5279 -2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2131 -2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9254 0.3007 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6852 -0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3957 0.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 -1.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1763 3.7998 0.0000 C 0 0 1 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 -5.0557 -2.9189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1762 1.6760 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3634 0.9906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9740 4.7515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 18 2 0 0 0 0 3 18 1 0 0 0 0 6 28 1 0 0 0 0 7 8 2 0 0 0 0 7 20 1 0 0 0 0 9 10 1 0 0 0 0 9 23 1 0 0 0 0 10 25 1 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 14 2 0 0 0 0 12 21 1 0 0 0 0 13 16 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 29 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 18 28 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 30 2 0 0 0 0 22 8 1 6 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 29 1 1 0 0 0 24 27 1 1 0 0 0 25 29 1 1 0 0 0 26 31 2 0 0 0 0 26 32 1 0 0 0 0 27 5 1 1 0 0 0 28 33 1 6 0 0 0 29 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.29
Volume:	495.256
LogP:	4.379
LogD:	3.829
LogS:	-4.598
# Rotatable Bonds:	7
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.463
Synthetic Accessibility Score:	5.167
Fsp3:	0.655
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.205
MDCK Permeability:	2.318785664101597e-05
Pgp-inhibitor:	0.072
Pgp-substrate:	0.101
Human Intestinal Absorption (HIA):	0.115
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.962
Plasma Protein Binding (PPB):	92.0995101928711%
Volume Distribution (VD):	0.384
Pgp-substrate:	7.1471266746521%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.374
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.697
CYP2C9-inhibitor:	0.207
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.324
CYP3A4-substrate:	0.89

ADMET: Excretion

Clearance (CL):	0.859
Half-life (T1/2):	0.531

ADMET: Toxicity

hERG Blockers:	0.136
Human Hepatotoxicity (H-HT):	0.624
Drug-inuced Liver Injury (DILI):	0.073
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.822
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.953
Carcinogencity:	0.818
Eye Corrosion:	0.074
Eye Irritation:	0.109
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC204341

Natural Product ID:	NPC204341
*Common Name:**	Norselic Acid A
IUPAC Name:	(8R,9S,10R,13S,14S,17R)-17-[(2R,5R)-5-ethyl-5-hydroxy-6-methylhept-6-en-2-yl]-10-methyl-3-oxo-8,9,11,12,14,15,16,17-octahydrocyclopenta[a]phenanthrene-13-carboxylic acid
Synonyms:
Standard InCHIKey:	RZICIXRISYIONZ-QEYQUZSWSA-N
Standard InCHI:	InChI=1S/C29H40O4/c1-6-28(33,18(2)3)15-11-19(4)23-9-10-25-22-8-7-20-17-21(30)12-14-27(20,5)24(22)13-16-29(23,25)26(31)32/h7-8,12,14,17,19,22-25,33H,2,6,9-11,13,15-16H2,1,3-5H3,(H,31,32)/t19-,22-,23-,24+,25+,27+,28-,29+/m1/s1
SMILES:	CC[C@@](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C(=O)O)(C(=C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1221577
PubChem CID:	44557570
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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	10

Activity Type	# Activity
NON-MOLECULAR	1
Organism	6
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	35.0	%	PMID[531700]
NPT2	Others	Unspecified		Activity	=	18.0	%	PMID[531700]
NPT2	Others	Unspecified		Activity	=	9.0	%	PMID[531700]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	8.0	mm	PMID[531700]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	2.5	uM	PMID[531700]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	0.0	mm	PMID[531700]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	8.0	mm	PMID[531700]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	9.0	mm	PMID[531700]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	IZ	=	8.0	mm	PMID[531700]

☑ 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 NPC204341 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	164
0.1-0.2	914
0.2-0.3	4433
0.3-0.4	12866
0.4-0.5	10351
0.5-0.6	7704
0.6-0.7	4592
0.7-0.8	1441
0.8-0.85	179
0.85-0.9	49
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9535	High Similarity	NPC262043
0.9438	High Similarity	NPC171395
0.9302	High Similarity	NPC136948
0.907	High Similarity	NPC29447
0.9059	High Similarity	NPC69279
0.9059	High Similarity	NPC83569
0.9059	High Similarity	NPC310470
0.8977	High Similarity	NPC72397
0.8953	High Similarity	NPC164577
0.8953	High Similarity	NPC87552
0.8925	High Similarity	NPC166745
0.8925	High Similarity	NPC235464
0.8889	High Similarity	NPC473986
0.8889	High Similarity	NPC474018
0.8837	High Similarity	NPC97913
0.8837	High Similarity	NPC470015
0.8837	High Similarity	NPC168188
0.8824	High Similarity	NPC201912
0.8824	High Similarity	NPC38350
0.8824	High Similarity	NPC477372
0.8764	High Similarity	NPC117122
0.875	High Similarity	NPC472869
0.8737	High Similarity	NPC99411
0.8736	High Similarity	NPC472865
0.8721	High Similarity	NPC320514
0.8721	High Similarity	NPC260956
0.8721	High Similarity	NPC142253
0.8721	High Similarity	NPC3511
0.871	High Similarity	NPC472941
0.871	High Similarity	NPC155676
0.871	High Similarity	NPC456
0.8652	High Similarity	NPC236618
0.8636	High Similarity	NPC8571
0.8636	High Similarity	NPC94531
0.8636	High Similarity	NPC269638
0.8636	High Similarity	NPC311702
0.8636	High Similarity	NPC123319
0.8621	High Similarity	NPC49019
0.8621	High Similarity	NPC3856
0.8621	High Similarity	NPC477373
0.8621	High Similarity	NPC279639
0.8605	High Similarity	NPC278459
0.8605	High Similarity	NPC147066
0.8588	High Similarity	NPC196827
0.8588	High Similarity	NPC477371
0.8588	High Similarity	NPC274996
0.8556	High Similarity	NPC472870
0.8539	High Similarity	NPC186975
0.8526	High Similarity	NPC197386
0.8526	High Similarity	NPC471717
0.8523	High Similarity	NPC19849
0.8523	High Similarity	NPC472864
0.8511	High Similarity	NPC250757
0.8511	High Similarity	NPC301534
0.8506	High Similarity	NPC469799
0.8506	High Similarity	NPC469806
0.8506	High Similarity	NPC472239
0.8506	High Similarity	NPC469805
0.8506	High Similarity	NPC469804
0.8506	High Similarity	NPC133391
0.8495	Intermediate Similarity	NPC469406
0.8471	Intermediate Similarity	NPC275494
0.8471	Intermediate Similarity	NPC179028
0.8471	Intermediate Similarity	NPC471409
0.8471	Intermediate Similarity	NPC74410
0.8462	Intermediate Similarity	NPC36668
0.8462	Intermediate Similarity	NPC214387
0.8462	Intermediate Similarity	NPC118011
0.8462	Intermediate Similarity	NPC66344
0.8444	Intermediate Similarity	NPC136548
0.8444	Intermediate Similarity	NPC128644
0.8444	Intermediate Similarity	NPC476293
0.8444	Intermediate Similarity	NPC476409
0.8438	Intermediate Similarity	NPC287833
0.8427	Intermediate Similarity	NPC473038
0.8427	Intermediate Similarity	NPC474537
0.8427	Intermediate Similarity	NPC11711
0.8421	Intermediate Similarity	NPC476253
0.8404	Intermediate Similarity	NPC174948
0.8404	Intermediate Similarity	NPC318282
0.8404	Intermediate Similarity	NPC476174
0.8404	Intermediate Similarity	NPC173875
0.8404	Intermediate Similarity	NPC469995
0.8387	Intermediate Similarity	NPC243866
0.8387	Intermediate Similarity	NPC152897
0.8387	Intermediate Similarity	NPC214697
0.8387	Intermediate Similarity	NPC66429
0.837	Intermediate Similarity	NPC472866
0.837	Intermediate Similarity	NPC477147
0.837	Intermediate Similarity	NPC477149
0.837	Intermediate Similarity	NPC469400
0.837	Intermediate Similarity	NPC129913
0.8353	Intermediate Similarity	NPC97377
0.8352	Intermediate Similarity	NPC48107
0.8351	Intermediate Similarity	NPC282524
0.8351	Intermediate Similarity	NPC472924
0.8333	Intermediate Similarity	NPC6247
0.8333	Intermediate Similarity	NPC186810
0.8316	Intermediate Similarity	NPC328371
0.8316	Intermediate Similarity	NPC249954
0.8316	Intermediate Similarity	NPC29152
0.8315	Intermediate Similarity	NPC473246
0.8315	Intermediate Similarity	NPC248758
0.8315	Intermediate Similarity	NPC165064
0.8315	Intermediate Similarity	NPC209882
0.8298	Intermediate Similarity	NPC8993
0.8298	Intermediate Similarity	NPC299100
0.8295	Intermediate Similarity	NPC296367
0.8295	Intermediate Similarity	NPC321289
0.8295	Intermediate Similarity	NPC100297
0.8295	Intermediate Similarity	NPC327969
0.8295	Intermediate Similarity	NPC472867
0.8295	Intermediate Similarity	NPC193347
0.8283	Intermediate Similarity	NPC472868
0.828	Intermediate Similarity	NPC212948
0.828	Intermediate Similarity	NPC45269
0.828	Intermediate Similarity	NPC19114
0.828	Intermediate Similarity	NPC475806
0.8276	Intermediate Similarity	NPC469798
0.8276	Intermediate Similarity	NPC469797
0.8265	Intermediate Similarity	NPC293753
0.8261	Intermediate Similarity	NPC77168
0.8261	Intermediate Similarity	NPC310236
0.8261	Intermediate Similarity	NPC84271
0.8261	Intermediate Similarity	NPC102414
0.8256	Intermediate Similarity	NPC189485
0.8247	Intermediate Similarity	NPC51370
0.8242	Intermediate Similarity	NPC93778
0.8242	Intermediate Similarity	NPC96496
0.8242	Intermediate Similarity	NPC287079
0.8235	Intermediate Similarity	NPC309399
0.8235	Intermediate Similarity	NPC180886
0.8229	Intermediate Similarity	NPC108078
0.8229	Intermediate Similarity	NPC107243
0.8229	Intermediate Similarity	NPC320306
0.8229	Intermediate Similarity	NPC156546
0.8222	Intermediate Similarity	NPC474083
0.8222	Intermediate Similarity	NPC142649
0.8222	Intermediate Similarity	NPC60350
0.8218	Intermediate Similarity	NPC220155
0.8211	Intermediate Similarity	NPC259286
0.8211	Intermediate Similarity	NPC180950
0.8211	Intermediate Similarity	NPC263347
0.8202	Intermediate Similarity	NPC472740
0.8202	Intermediate Similarity	NPC167103
0.8202	Intermediate Similarity	NPC477852
0.8202	Intermediate Similarity	NPC102197
0.8191	Intermediate Similarity	NPC472930
0.8191	Intermediate Similarity	NPC472942
0.8191	Intermediate Similarity	NPC474736
0.8191	Intermediate Similarity	NPC474807
0.8191	Intermediate Similarity	NPC250575
0.8191	Intermediate Similarity	NPC472871
0.8182	Intermediate Similarity	NPC142244
0.8182	Intermediate Similarity	NPC471898
0.8182	Intermediate Similarity	NPC72151
0.8172	Intermediate Similarity	NPC46281
0.8172	Intermediate Similarity	NPC69622
0.8163	Intermediate Similarity	NPC302537
0.8163	Intermediate Similarity	NPC163372
0.8163	Intermediate Similarity	NPC224720
0.8163	Intermediate Similarity	NPC146822
0.8163	Intermediate Similarity	NPC476240
0.8163	Intermediate Similarity	NPC476223
0.8161	Intermediate Similarity	NPC215843
0.8152	Intermediate Similarity	NPC44181
0.8152	Intermediate Similarity	NPC249889
0.8152	Intermediate Similarity	NPC193843
0.8144	Intermediate Similarity	NPC48647
0.8144	Intermediate Similarity	NPC57079
0.8144	Intermediate Similarity	NPC103051
0.8144	Intermediate Similarity	NPC108368
0.814	Intermediate Similarity	NPC165711
0.8132	Intermediate Similarity	NPC222613
0.8132	Intermediate Similarity	NPC118648
0.8132	Intermediate Similarity	NPC89077
0.8132	Intermediate Similarity	NPC475022
0.8119	Intermediate Similarity	NPC91034
0.8118	Intermediate Similarity	NPC476795
0.8111	Intermediate Similarity	NPC16287
0.8111	Intermediate Similarity	NPC181743
0.8111	Intermediate Similarity	NPC144258
0.8111	Intermediate Similarity	NPC320801
0.8111	Intermediate Similarity	NPC214043
0.8111	Intermediate Similarity	NPC85774
0.8111	Intermediate Similarity	NPC178025
0.8111	Intermediate Similarity	NPC96095
0.8105	Intermediate Similarity	NPC7165
0.8105	Intermediate Similarity	NPC166906
0.8105	Intermediate Similarity	NPC184870
0.809	Intermediate Similarity	NPC238991
0.809	Intermediate Similarity	NPC302661
0.8085	Intermediate Similarity	NPC470113
0.8085	Intermediate Similarity	NPC473998
0.8085	Intermediate Similarity	NPC476187
0.8081	Intermediate Similarity	NPC308726
0.8081	Intermediate Similarity	NPC320447
0.8081	Intermediate Similarity	NPC234892
0.8081	Intermediate Similarity	NPC204450
0.8081	Intermediate Similarity	NPC119601

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 NPC204341 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1180
0.2-0.3	3689
0.3-0.4	2763
0.4-0.5	838
0.5-0.6	225
0.6-0.7	168
0.7-0.8	118
0.8-0.85	14
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9101	High Similarity	NPD5284	Approved
0.9101	High Similarity	NPD5281	Approved
0.8539	High Similarity	NPD4694	Approved
0.8539	High Similarity	NPD5690	Phase 2
0.8539	High Similarity	NPD5280	Approved
0.8478	Intermediate Similarity	NPD5694	Approved
0.8478	Intermediate Similarity	NPD6050	Approved
0.837	Intermediate Similarity	NPD5207	Approved
0.837	Intermediate Similarity	NPD5692	Phase 3
0.8295	Intermediate Similarity	NPD4223	Phase 3
0.8295	Intermediate Similarity	NPD4221	Approved
0.8247	Intermediate Similarity	NPD6404	Discontinued
0.8222	Intermediate Similarity	NPD5329	Approved
0.8211	Intermediate Similarity	NPD5695	Phase 3
0.8132	Intermediate Similarity	NPD5279	Phase 3
0.8111	Intermediate Similarity	NPD4197	Approved
0.8065	Intermediate Similarity	NPD6080	Approved
0.8065	Intermediate Similarity	NPD6904	Approved
0.8065	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6673	Approved
0.8041	Intermediate Similarity	NPD6083	Phase 2
0.8041	Intermediate Similarity	NPD6084	Phase 2
0.8	Intermediate Similarity	NPD4687	Approved
0.8	Intermediate Similarity	NPD5733	Approved
0.7979	Intermediate Similarity	NPD4096	Approved
0.7957	Intermediate Similarity	NPD6672	Approved
0.7957	Intermediate Similarity	NPD5737	Approved
0.7957	Intermediate Similarity	NPD4518	Approved
0.7955	Intermediate Similarity	NPD4195	Approved
0.7935	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD4138	Approved
0.7935	Intermediate Similarity	NPD4689	Approved
0.7935	Intermediate Similarity	NPD4693	Phase 3
0.7935	Intermediate Similarity	NPD4623	Approved
0.7935	Intermediate Similarity	NPD4519	Discontinued
0.7935	Intermediate Similarity	NPD4690	Approved
0.7935	Intermediate Similarity	NPD5205	Approved
0.7935	Intermediate Similarity	NPD4688	Approved
0.7895	Intermediate Similarity	NPD6079	Approved
0.7895	Intermediate Similarity	NPD5693	Phase 1
0.7872	Intermediate Similarity	NPD4753	Phase 2
0.7835	Intermediate Similarity	NPD5654	Approved
0.7835	Intermediate Similarity	NPD4629	Approved
0.7835	Intermediate Similarity	NPD5210	Approved
0.7812	Intermediate Similarity	NPD6399	Phase 3
0.7812	Intermediate Similarity	NPD5133	Approved
0.7791	Intermediate Similarity	NPD4058	Approved
0.7778	Intermediate Similarity	NPD5696	Approved
0.7766	Intermediate Similarity	NPD5208	Approved
0.7765	Intermediate Similarity	NPD5276	Approved
0.7742	Intermediate Similarity	NPD6684	Approved
0.7742	Intermediate Similarity	NPD7334	Approved
0.7742	Intermediate Similarity	NPD7146	Approved
0.7742	Intermediate Similarity	NPD7521	Approved
0.7742	Intermediate Similarity	NPD5330	Approved
0.7742	Intermediate Similarity	NPD6409	Approved
0.7742	Intermediate Similarity	NPD6098	Approved
0.7723	Intermediate Similarity	NPD5211	Phase 2
0.7717	Intermediate Similarity	NPD4786	Approved
0.7717	Intermediate Similarity	NPD3133	Approved
0.7717	Intermediate Similarity	NPD3666	Approved
0.7717	Intermediate Similarity	NPD3665	Phase 1
0.7692	Intermediate Similarity	NPD6899	Approved
0.7692	Intermediate Similarity	NPD6881	Approved
0.7684	Intermediate Similarity	NPD5328	Approved
0.7677	Intermediate Similarity	NPD5959	Approved
0.7667	Intermediate Similarity	NPD4695	Discontinued
0.7653	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD3617	Approved
0.7596	Intermediate Similarity	NPD5697	Approved
0.7582	Intermediate Similarity	NPD4692	Approved
0.7582	Intermediate Similarity	NPD4139	Approved
0.7579	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD6903	Approved
0.7576	Intermediate Similarity	NPD5221	Approved
0.7576	Intermediate Similarity	NPD5222	Approved
0.7576	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD5141	Approved
0.7553	Intermediate Similarity	NPD3618	Phase 1
0.7547	Intermediate Similarity	NPD7290	Approved
0.7547	Intermediate Similarity	NPD6883	Approved
0.7547	Intermediate Similarity	NPD7102	Approved
0.7526	Intermediate Similarity	NPD7515	Phase 2
0.7525	Intermediate Similarity	NPD5286	Approved
0.7525	Intermediate Similarity	NPD4696	Approved
0.7525	Intermediate Similarity	NPD5285	Approved
0.7524	Intermediate Similarity	NPD6011	Approved
0.75	Intermediate Similarity	NPD5739	Approved
0.75	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD3667	Approved
0.75	Intermediate Similarity	NPD5173	Approved
0.75	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD6402	Approved
0.7477	Intermediate Similarity	NPD6650	Approved
0.7477	Intermediate Similarity	NPD6617	Approved
0.7477	Intermediate Similarity	NPD6869	Approved
0.7477	Intermediate Similarity	NPD6649	Approved
0.7477	Intermediate Similarity	NPD6847	Approved
0.7477	Intermediate Similarity	NPD8130	Phase 1
0.7474	Intermediate Similarity	NPD3573	Approved
0.7455	Intermediate Similarity	NPD7115	Discovery
0.7453	Intermediate Similarity	NPD6014	Approved
0.7453	Intermediate Similarity	NPD6012	Approved
0.7453	Intermediate Similarity	NPD6013	Approved
0.7451	Intermediate Similarity	NPD5223	Approved
0.7449	Intermediate Similarity	NPD4202	Approved
0.7444	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4747	Approved
0.7442	Intermediate Similarity	NPD4691	Approved
0.7419	Intermediate Similarity	NPD4788	Approved
0.7407	Intermediate Similarity	NPD8297	Approved
0.7407	Intermediate Similarity	NPD6882	Approved
0.74	Intermediate Similarity	NPD7614	Phase 1
0.7379	Intermediate Similarity	NPD5225	Approved
0.7379	Intermediate Similarity	NPD5091	Approved
0.7379	Intermediate Similarity	NPD5226	Approved
0.7379	Intermediate Similarity	NPD5224	Approved
0.7379	Intermediate Similarity	NPD4633	Approved
0.7374	Intermediate Similarity	NPD6001	Approved
0.7374	Intermediate Similarity	NPD7748	Approved
0.7358	Intermediate Similarity	NPD7320	Approved
0.7327	Intermediate Similarity	NPD4755	Approved
0.7326	Intermediate Similarity	NPD4137	Phase 3
0.7308	Intermediate Similarity	NPD5175	Approved
0.7308	Intermediate Similarity	NPD5174	Approved
0.729	Intermediate Similarity	NPD6373	Approved
0.729	Intermediate Similarity	NPD6372	Approved
0.7264	Intermediate Similarity	NPD6614	Approved
0.7264	Intermediate Similarity	NPD5701	Approved
0.7234	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4697	Phase 3
0.7191	Intermediate Similarity	NPD4784	Approved
0.7191	Intermediate Similarity	NPD4785	Approved
0.7184	Intermediate Similarity	NPD7640	Approved
0.7184	Intermediate Similarity	NPD7639	Approved
0.7184	Intermediate Similarity	NPD4700	Approved
0.7182	Intermediate Similarity	NPD4632	Approved
0.7172	Intermediate Similarity	NPD6411	Approved
0.7159	Intermediate Similarity	NPD4243	Approved
0.7158	Intermediate Similarity	NPD3668	Phase 3
0.7157	Intermediate Similarity	NPD7902	Approved
0.7156	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6052	Approved
0.7128	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7638	Approved
0.7083	Intermediate Similarity	NPD5363	Approved
0.7083	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6335	Approved
0.7071	Intermediate Similarity	NPD5785	Approved
0.7054	Intermediate Similarity	NPD6868	Approved
0.7037	Intermediate Similarity	NPD4729	Approved
0.7037	Intermediate Similarity	NPD4730	Approved
0.7018	Intermediate Similarity	NPD7101	Approved
0.7018	Intermediate Similarity	NPD7100	Approved
0.7	Intermediate Similarity	NPD7637	Suspended
0.6991	Remote Similarity	NPD6317	Approved
0.6991	Remote Similarity	NPD6009	Approved
0.6981	Remote Similarity	NPD4754	Approved
0.697	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6101	Approved
0.6966	Remote Similarity	NPD6081	Approved
0.6931	Remote Similarity	NPD5779	Approved
0.6931	Remote Similarity	NPD5778	Approved
0.693	Remote Similarity	NPD6314	Approved
0.693	Remote Similarity	NPD6313	Approved
0.6909	Remote Similarity	NPD4634	Approved
0.6909	Remote Similarity	NPD5249	Phase 3
0.6909	Remote Similarity	NPD5169	Approved
0.6909	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5251	Approved
0.6909	Remote Similarity	NPD5248	Approved
0.6909	Remote Similarity	NPD5247	Approved
0.6909	Remote Similarity	NPD5135	Approved
0.6909	Remote Similarity	NPD5250	Approved
0.6907	Remote Similarity	NPD1694	Approved
0.6903	Remote Similarity	NPD6274	Approved
0.6893	Remote Similarity	NPD7732	Phase 3
0.6881	Remote Similarity	NPD5168	Approved
0.6881	Remote Similarity	NPD5128	Approved
0.6875	Remote Similarity	NPD5362	Discontinued
0.6863	Remote Similarity	NPD7900	Approved
0.6863	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4768	Approved
0.6852	Remote Similarity	NPD4767	Approved
0.6852	Remote Similarity	NPD6008	Approved
0.6847	Remote Similarity	NPD5127	Approved
0.6847	Remote Similarity	NPD5215	Approved
0.6847	Remote Similarity	NPD5217	Approved
0.6847	Remote Similarity	NPD5216	Approved
0.6832	Remote Similarity	NPD8035	Phase 2
0.6832	Remote Similarity	NPD8034	Phase 2
0.6818	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6926	Approved
0.6813	Remote Similarity	NPD6924	Approved
0.681	Remote Similarity	NPD6319	Approved
0.68	Remote Similarity	NPD6051	Approved
0.6789	Remote Similarity	NPD6412	Phase 2
0.6782	Remote Similarity	NPD4224	Phase 2
0.6782	Remote Similarity	NPD7331	Phase 2
0.678	Remote Similarity	NPD7604	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