NPASS Compound

Structure

NPC136948 OpenBabel07101718302D 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 1 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 1 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:	456.32
Volume:	500.529
LogP:	5.074
LogD:	4.748
LogS:	-4.48
# 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:	0.439
Synthetic Accessibility Score:	4.92
Fsp3:	0.793
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:	-5.166
MDCK Permeability:	1.4944959730200935e-05
Pgp-inhibitor:	0.277
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.944
30% Bioavailability (F30%):	0.185

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.862
Plasma Protein Binding (PPB):	90.13172149658203%
Volume Distribution (VD):	0.555
Pgp-substrate:	2.5120110511779785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.527
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.189
CYP2C9-substrate:	0.809
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.235
CYP3A4-inhibitor:	0.4
CYP3A4-substrate:	0.244

ADMET: Excretion

Clearance (CL):	2.808
Half-life (T1/2):	0.629

ADMET: Toxicity

hERG Blockers:	0.126
Human Hepatotoxicity (H-HT):	0.509
Drug-inuced Liver Injury (DILI):	0.564
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.16
Skin Sensitization:	0.92
Carcinogencity:	0.525
Eye Corrosion:	0.82
Eye Irritation:	0.158
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC136948

Natural Product ID:	NPC136948
*Common Name:**	Norselic Acid D
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-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-13-carboxylic acid
Synonyms:	Norselic Acid D
Standard InCHIKey:	FQQBBMUNHBMJPB-QEYQUZSWSA-N
Standard InCHI:	InChI=1S/C29H44O4/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/h17,19,22-25,33H,2,6-16H2,1,3-5H3,(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]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C(=O)O)(C(=C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1221414
PubChem CID:	44557651
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	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	=	2.0	uM	PMID[469400]

☑ 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 NPC136948 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	159
0.1-0.2	1056
0.2-0.3	5033
0.3-0.4	14323
0.4-0.5	8154
0.5-0.6	6520
0.6-0.7	4898
0.7-0.8	2156
0.8-0.85	307
0.85-0.9	77
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9759	High Similarity	NPC262043
0.9383	High Similarity	NPC320514
0.9302	High Similarity	NPC204341
0.9277	High Similarity	NPC29447
0.9259	High Similarity	NPC477372
0.9259	High Similarity	NPC147066
0.9176	High Similarity	NPC117122
0.9167	High Similarity	NPC472869
0.9157	High Similarity	NPC164577
0.9048	High Similarity	NPC269638
0.9036	High Similarity	NPC470015
0.9036	High Similarity	NPC97913
0.9036	High Similarity	NPC477373
0.9036	High Similarity	NPC168188
0.9024	High Similarity	NPC278459
0.9024	High Similarity	NPC201912
0.9024	High Similarity	NPC38350
0.9012	High Similarity	NPC477371
0.8953	High Similarity	NPC472870
0.8941	High Similarity	NPC186975
0.8929	High Similarity	NPC19849
0.8929	High Similarity	NPC472865
0.8929	High Similarity	NPC472864
0.8916	High Similarity	NPC260956
0.8916	High Similarity	NPC133391
0.8916	High Similarity	NPC472239
0.8916	High Similarity	NPC193347
0.8837	High Similarity	NPC236618
0.8837	High Similarity	NPC128644
0.8837	High Similarity	NPC476409
0.8837	High Similarity	NPC96496
0.8824	High Similarity	NPC123319
0.8824	High Similarity	NPC94531
0.8824	High Similarity	NPC311702
0.881	High Similarity	NPC83569
0.881	High Similarity	NPC310470
0.881	High Similarity	NPC69279
0.8795	High Similarity	NPC471898
0.878	High Similarity	NPC215843
0.8778	High Similarity	NPC171395
0.8778	High Similarity	NPC476174
0.8765	High Similarity	NPC165711
0.875	High Similarity	NPC472866
0.8736	High Similarity	NPC48107
0.8706	High Similarity	NPC144258
0.8706	High Similarity	NPC165064
0.8706	High Similarity	NPC248758
0.8706	High Similarity	NPC85774
0.8706	High Similarity	NPC214043
0.8706	High Similarity	NPC96095
0.869	High Similarity	NPC142253
0.869	High Similarity	NPC3511
0.869	High Similarity	NPC472867
0.8681	High Similarity	NPC29152
0.8681	High Similarity	NPC472941
0.8681	High Similarity	NPC456
0.8675	High Similarity	NPC37038
0.8667	High Similarity	NPC8993
0.8659	High Similarity	NPC179028
0.8659	High Similarity	NPC471409
0.8659	High Similarity	NPC275494
0.8652	High Similarity	NPC473986
0.8652	High Similarity	NPC475806
0.8652	High Similarity	NPC474018
0.8652	High Similarity	NPC473998
0.8642	High Similarity	NPC180886
0.8636	High Similarity	NPC214387
0.8636	High Similarity	NPC66344
0.8636	High Similarity	NPC305039
0.8636	High Similarity	NPC473999
0.8636	High Similarity	NPC474570
0.8636	High Similarity	NPC309603
0.8605	High Similarity	NPC8571
0.8605	High Similarity	NPC11711
0.8605	High Similarity	NPC469948
0.8605	High Similarity	NPC473038
0.8605	High Similarity	NPC60350
0.8605	High Similarity	NPC471224
0.8588	High Similarity	NPC167103
0.8588	High Similarity	NPC477852
0.8588	High Similarity	NPC49019
0.8588	High Similarity	NPC472740
0.8587	High Similarity	NPC156546
0.8587	High Similarity	NPC107243
0.8571	High Similarity	NPC173875
0.8571	High Similarity	NPC469995
0.8571	High Similarity	NPC174948
0.8571	High Similarity	NPC318282
0.8556	High Similarity	NPC472871
0.8556	High Similarity	NPC243866
0.8554	High Similarity	NPC231431
0.8554	High Similarity	NPC158846
0.8539	High Similarity	NPC477147
0.8539	High Similarity	NPC469400
0.8539	High Similarity	NPC48010
0.8539	High Similarity	NPC477149
0.8537	High Similarity	NPC66105
0.8537	High Similarity	NPC97377
0.8537	High Similarity	NPC61952
0.8523	High Similarity	NPC72397
0.8506	High Similarity	NPC145879
0.8506	High Similarity	NPC474778
0.8506	High Similarity	NPC474733
0.8506	High Similarity	NPC469994
0.8506	High Similarity	NPC155011
0.8506	High Similarity	NPC31564
0.8506	High Similarity	NPC474732
0.8495	Intermediate Similarity	NPC235464
0.8495	Intermediate Similarity	NPC197386
0.8495	Intermediate Similarity	NPC166745
0.8488	Intermediate Similarity	NPC473246
0.8488	Intermediate Similarity	NPC16287
0.8488	Intermediate Similarity	NPC87552
0.8488	Intermediate Similarity	NPC181743
0.8488	Intermediate Similarity	NPC209882
0.8488	Intermediate Similarity	NPC194937
0.8488	Intermediate Similarity	NPC237712
0.8488	Intermediate Similarity	NPC178025
0.8488	Intermediate Similarity	NPC476038
0.8478	Intermediate Similarity	NPC155676
0.8478	Intermediate Similarity	NPC328371
0.8471	Intermediate Similarity	NPC321289
0.8471	Intermediate Similarity	NPC327969
0.8471	Intermediate Similarity	NPC100297
0.8444	Intermediate Similarity	NPC476187
0.8444	Intermediate Similarity	NPC470113
0.8444	Intermediate Similarity	NPC154101
0.8434	Intermediate Similarity	NPC110094
0.8434	Intermediate Similarity	NPC198240
0.8434	Intermediate Similarity	NPC280654
0.8434	Intermediate Similarity	NPC321514
0.8434	Intermediate Similarity	NPC74410
0.8434	Intermediate Similarity	NPC260385
0.8427	Intermediate Similarity	NPC477943
0.8427	Intermediate Similarity	NPC310010
0.8427	Intermediate Similarity	NPC326627
0.8427	Intermediate Similarity	NPC1015
0.8427	Intermediate Similarity	NPC31985
0.8427	Intermediate Similarity	NPC2983
0.8427	Intermediate Similarity	NPC475921
0.8427	Intermediate Similarity	NPC476733
0.8427	Intermediate Similarity	NPC215029
0.8427	Intermediate Similarity	NPC474704
0.8415	Intermediate Similarity	NPC246445
0.8409	Intermediate Similarity	NPC90652
0.8409	Intermediate Similarity	NPC475740
0.8409	Intermediate Similarity	NPC474684
0.8409	Intermediate Similarity	NPC142361
0.8409	Intermediate Similarity	NPC93778
0.8409	Intermediate Similarity	NPC58063
0.8409	Intermediate Similarity	NPC317590
0.8404	Intermediate Similarity	NPC287833
0.8404	Intermediate Similarity	NPC51370
0.8391	Intermediate Similarity	NPC474083
0.8391	Intermediate Similarity	NPC283733
0.8391	Intermediate Similarity	NPC474537
0.8391	Intermediate Similarity	NPC142649
0.8387	Intermediate Similarity	NPC475894
0.8387	Intermediate Similarity	NPC57416
0.8387	Intermediate Similarity	NPC108078
0.8387	Intermediate Similarity	NPC253826
0.8387	Intermediate Similarity	NPC476253
0.8387	Intermediate Similarity	NPC320306
0.8372	Intermediate Similarity	NPC3856
0.8372	Intermediate Similarity	NPC279639
0.8372	Intermediate Similarity	NPC105803
0.837	Intermediate Similarity	NPC271195
0.8353	Intermediate Similarity	NPC162632
0.8353	Intermediate Similarity	NPC274050
0.8353	Intermediate Similarity	NPC267691
0.8353	Intermediate Similarity	NPC263272
0.8353	Intermediate Similarity	NPC142244
0.8352	Intermediate Similarity	NPC472930
0.8352	Intermediate Similarity	NPC476416
0.8352	Intermediate Similarity	NPC474807
0.8352	Intermediate Similarity	NPC474736
0.8333	Intermediate Similarity	NPC196827
0.8333	Intermediate Similarity	NPC476369
0.8333	Intermediate Similarity	NPC192744
0.8333	Intermediate Similarity	NPC274996
0.8333	Intermediate Similarity	NPC476437
0.8333	Intermediate Similarity	NPC199595
0.8333	Intermediate Similarity	NPC471896
0.8333	Intermediate Similarity	NPC320026
0.8333	Intermediate Similarity	NPC192329
0.8316	Intermediate Similarity	NPC163372
0.8316	Intermediate Similarity	NPC302537
0.8316	Intermediate Similarity	NPC99411
0.8316	Intermediate Similarity	NPC472924
0.8315	Intermediate Similarity	NPC470417
0.8313	Intermediate Similarity	NPC212661
0.8313	Intermediate Similarity	NPC471035
0.8313	Intermediate Similarity	NPC266193
0.8313	Intermediate Similarity	NPC471899
0.8313	Intermediate Similarity	NPC472300
0.8313	Intermediate Similarity	NPC471897
0.8313	Intermediate Similarity	NPC257666
0.8313	Intermediate Similarity	NPC107039
0.8298	Intermediate Similarity	NPC471717
0.8295	Intermediate Similarity	NPC322159

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 NPC136948 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	1342
0.2-0.3	3982
0.3-0.4	2497
0.4-0.5	689
0.5-0.6	173
0.6-0.7	128
0.7-0.8	134
0.8-0.85	41
0.85-0.9	18
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8916	High Similarity	NPD4221	Approved
0.8916	High Similarity	NPD4223	Phase 3
0.8824	High Similarity	NPD5329	Approved
0.8706	High Similarity	NPD4197	Approved
0.8652	High Similarity	NPD5281	Approved
0.8652	High Similarity	NPD5284	Approved
0.8636	High Similarity	NPD6673	Approved
0.8636	High Similarity	NPD6080	Approved
0.8636	High Similarity	NPD6904	Approved
0.8587	High Similarity	NPD6084	Phase 2
0.8587	High Similarity	NPD6083	Phase 2
0.8523	High Similarity	NPD5737	Approved
0.8523	High Similarity	NPD6672	Approved
0.8506	High Similarity	NPD5205	Approved
0.8506	High Similarity	NPD4688	Approved
0.8506	High Similarity	NPD4689	Approved
0.8506	High Similarity	NPD4693	Phase 3
0.8506	High Similarity	NPD4690	Approved
0.8506	High Similarity	NPD4138	Approved
0.8444	Intermediate Similarity	NPD5693	Phase 1
0.8427	Intermediate Similarity	NPD4753	Phase 2
0.837	Intermediate Similarity	NPD5695	Phase 3
0.8352	Intermediate Similarity	NPD6399	Phase 3
0.8315	Intermediate Similarity	NPD5208	Approved
0.8298	Intermediate Similarity	NPD5696	Approved
0.8295	Intermediate Similarity	NPD4519	Discontinued
0.8295	Intermediate Similarity	NPD7334	Approved
0.8295	Intermediate Similarity	NPD6098	Approved
0.8295	Intermediate Similarity	NPD4694	Approved
0.8295	Intermediate Similarity	NPD6684	Approved
0.8295	Intermediate Similarity	NPD7521	Approved
0.8295	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD7146	Approved
0.8295	Intermediate Similarity	NPD5280	Approved
0.8295	Intermediate Similarity	NPD5330	Approved
0.8295	Intermediate Similarity	NPD4623	Approved
0.8295	Intermediate Similarity	NPD5690	Phase 2
0.8295	Intermediate Similarity	NPD6409	Approved
0.8276	Intermediate Similarity	NPD3666	Approved
0.8276	Intermediate Similarity	NPD3133	Approved
0.8276	Intermediate Similarity	NPD3665	Phase 1
0.8276	Intermediate Similarity	NPD4786	Approved
0.8242	Intermediate Similarity	NPD6050	Approved
0.8222	Intermediate Similarity	NPD5328	Approved
0.8214	Intermediate Similarity	NPD3617	Approved
0.8172	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.8132	Intermediate Similarity	NPD5692	Phase 3
0.8118	Intermediate Similarity	NPD4195	Approved
0.8111	Intermediate Similarity	NPD6903	Approved
0.8111	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD3618	Phase 1
0.8046	Intermediate Similarity	NPD3667	Approved
0.8043	Intermediate Similarity	NPD5694	Approved
0.8043	Intermediate Similarity	NPD6079	Approved
0.8043	Intermediate Similarity	NPD7515	Phase 2
0.8025	Intermediate Similarity	NPD4747	Approved
0.8023	Intermediate Similarity	NPD4695	Discontinued
0.8022	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.798	Intermediate Similarity	NPD7128	Approved
0.798	Intermediate Similarity	NPD6402	Approved
0.798	Intermediate Similarity	NPD5739	Approved
0.798	Intermediate Similarity	NPD6675	Approved
0.7979	Intermediate Similarity	NPD5210	Approved
0.7979	Intermediate Similarity	NPD4629	Approved
0.7957	Intermediate Similarity	NPD4202	Approved
0.7935	Intermediate Similarity	NPD5207	Approved
0.7901	Intermediate Similarity	NPD4137	Phase 3
0.7889	Intermediate Similarity	NPD5279	Phase 3
0.7872	Intermediate Similarity	NPD7748	Approved
0.7872	Intermediate Similarity	NPD6001	Approved
0.7857	Intermediate Similarity	NPD5211	Phase 2
0.7835	Intermediate Similarity	NPD6404	Discontinued
0.7822	Intermediate Similarity	NPD6899	Approved
0.7822	Intermediate Similarity	NPD6881	Approved
0.7822	Intermediate Similarity	NPD7320	Approved
0.7812	Intermediate Similarity	NPD4755	Approved
0.7805	Intermediate Similarity	NPD4691	Approved
0.7753	Intermediate Similarity	NPD4788	Approved
0.7745	Intermediate Similarity	NPD6372	Approved
0.7745	Intermediate Similarity	NPD6373	Approved
0.7742	Intermediate Similarity	NPD4096	Approved
0.7738	Intermediate Similarity	NPD5733	Approved
0.7727	Intermediate Similarity	NPD4139	Approved
0.7727	Intermediate Similarity	NPD4692	Approved
0.7723	Intermediate Similarity	NPD5697	Approved
0.7723	Intermediate Similarity	NPD5701	Approved
0.7711	Intermediate Similarity	NPD4243	Approved
0.7708	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD5221	Approved
0.7708	Intermediate Similarity	NPD5222	Approved
0.7708	Intermediate Similarity	NPD4697	Phase 3
0.77	Intermediate Similarity	NPD5141	Approved
0.767	Intermediate Similarity	NPD6883	Approved
0.767	Intermediate Similarity	NPD7102	Approved
0.767	Intermediate Similarity	NPD7290	Approved
0.7667	Intermediate Similarity	NPD3668	Phase 3
0.7653	Intermediate Similarity	NPD5285	Approved
0.7653	Intermediate Similarity	NPD7640	Approved
0.7653	Intermediate Similarity	NPD7639	Approved
0.7653	Intermediate Similarity	NPD4700	Approved
0.7653	Intermediate Similarity	NPD5286	Approved
0.7653	Intermediate Similarity	NPD4696	Approved
0.7647	Intermediate Similarity	NPD6011	Approved
0.7629	Intermediate Similarity	NPD5173	Approved
0.7629	Intermediate Similarity	NPD7902	Approved
0.7609	Intermediate Similarity	NPD3573	Approved
0.7604	Intermediate Similarity	NPD5654	Approved
0.76	Intermediate Similarity	NPD6052	Approved
0.7596	Intermediate Similarity	NPD6649	Approved
0.7596	Intermediate Similarity	NPD8130	Phase 1
0.7596	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD6847	Approved
0.7596	Intermediate Similarity	NPD6650	Approved
0.7596	Intermediate Similarity	NPD6617	Approved
0.7596	Intermediate Similarity	NPD6869	Approved
0.7586	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD5133	Approved
0.7576	Intermediate Similarity	NPD5223	Approved
0.7573	Intermediate Similarity	NPD6012	Approved
0.7573	Intermediate Similarity	NPD6014	Approved
0.7573	Intermediate Similarity	NPD6013	Approved
0.757	Intermediate Similarity	NPD7115	Discovery
0.7551	Intermediate Similarity	NPD7638	Approved
0.7529	Intermediate Similarity	NPD4687	Approved
0.7529	Intermediate Similarity	NPD4784	Approved
0.7529	Intermediate Similarity	NPD4785	Approved
0.7529	Intermediate Similarity	NPD4058	Approved
0.7527	Intermediate Similarity	NPD4518	Approved
0.7526	Intermediate Similarity	NPD7614	Phase 1
0.7524	Intermediate Similarity	NPD6882	Approved
0.7524	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD5225	Approved
0.75	Intermediate Similarity	NPD5091	Approved
0.75	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD5226	Approved
0.75	Intermediate Similarity	NPD6081	Approved
0.75	Intermediate Similarity	NPD5276	Approved
0.75	Intermediate Similarity	NPD5224	Approved
0.7449	Intermediate Similarity	NPD5959	Approved
0.7444	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD5174	Approved
0.7426	Intermediate Similarity	NPD5175	Approved
0.7426	Intermediate Similarity	NPD4754	Approved
0.7379	Intermediate Similarity	NPD6614	Approved
0.7349	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7900	Approved
0.732	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4224	Phase 2
0.7292	Intermediate Similarity	NPD8034	Phase 2
0.7292	Intermediate Similarity	NPD8035	Phase 2
0.729	Intermediate Similarity	NPD4632	Approved
0.7282	Intermediate Similarity	NPD4768	Approved
0.7282	Intermediate Similarity	NPD6008	Approved
0.7282	Intermediate Similarity	NPD4767	Approved
0.7263	Intermediate Similarity	NPD6051	Approved
0.7241	Intermediate Similarity	NPD5275	Approved
0.7241	Intermediate Similarity	NPD7339	Approved
0.7241	Intermediate Similarity	NPD6942	Approved
0.7241	Intermediate Similarity	NPD4190	Phase 3
0.7222	Intermediate Similarity	NPD7525	Registered
0.7212	Intermediate Similarity	NPD6412	Phase 2
0.7182	Intermediate Similarity	NPD6335	Approved
0.7156	Intermediate Similarity	NPD6274	Approved
0.7156	Intermediate Similarity	NPD6868	Approved
0.7143	Intermediate Similarity	NPD5360	Phase 3
0.7143	Intermediate Similarity	NPD5128	Approved
0.7143	Intermediate Similarity	NPD4730	Approved
0.7143	Intermediate Similarity	NPD4729	Approved
0.7143	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7100	Approved
0.7117	Intermediate Similarity	NPD7101	Approved
0.7108	Intermediate Similarity	NPD7331	Phase 2
0.7091	Intermediate Similarity	NPD6009	Approved
0.7091	Intermediate Similarity	NPD6317	Approved
0.7027	Intermediate Similarity	NPD6314	Approved
0.7027	Intermediate Similarity	NPD6313	Approved
0.7021	Intermediate Similarity	NPD5363	Approved
0.701	Intermediate Similarity	NPD5785	Approved
0.7009	Intermediate Similarity	NPD4634	Approved
0.7009	Intermediate Similarity	NPD5248	Approved
0.7009	Intermediate Similarity	NPD5249	Phase 3
0.7009	Intermediate Similarity	NPD5247	Approved
0.7009	Intermediate Similarity	NPD5135	Approved
0.7009	Intermediate Similarity	NPD5169	Approved
0.7009	Intermediate Similarity	NPD5251	Approved
0.7009	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5250	Approved
0.7	Intermediate Similarity	NPD7732	Phase 3
0.6991	Remote Similarity	NPD6908	Approved
0.6991	Remote Similarity	NPD6909	Approved
0.699	Remote Similarity	NPD7632	Discontinued
0.6989	Remote Similarity	NPD5362	Discontinued
0.6988	Remote Similarity	NPD7341	Phase 2
0.6981	Remote Similarity	NPD5168	Approved
0.6966	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6117	Approved
0.6944	Remote Similarity	NPD5216	Approved
0.6944	Remote Similarity	NPD5127	Approved
0.6944	Remote Similarity	NPD5215	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data