NPASS Compound

Structure

NPC262043 OpenBabel07101718252D 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 1 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 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 1 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 1 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:	5.629
LogD:	4.876
LogS:	-4.69
# 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:	0.448
Synthetic Accessibility Score:	5.008
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:	-5.141
MDCK Permeability:	2.2528025510837324e-05
Pgp-inhibitor:	0.114
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.033
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.443
Plasma Protein Binding (PPB):	89.53485870361328%
Volume Distribution (VD):	0.498
Pgp-substrate:	3.093165636062622%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.508
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.714
CYP2C9-inhibitor:	0.162
CYP2C9-substrate:	0.189
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.763
CYP3A4-substrate:	0.481

ADMET: Excretion

Clearance (CL):	2.256
Half-life (T1/2):	0.335

ADMET: Toxicity

hERG Blockers:	0.211
Human Hepatotoxicity (H-HT):	0.629
Drug-inuced Liver Injury (DILI):	0.477
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.34
Maximum Recommended Daily Dose:	0.727
Skin Sensitization:	0.968
Carcinogencity:	0.795
Eye Corrosion:	0.196
Eye Irritation:	0.095
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC262043

Natural Product ID:	NPC262043
*Common Name:**	Norselic Acid B
IUPAC Name:	(5S,8R,9S,10R,13S,14S,17R)-17-[(2R,5R)-5-ethyl-5-hydroxy-6-methylhept-6-en-2-yl]-10-methyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-13-carboxylic acid
Synonyms:
Standard InCHIKey:	KTOLWQCZNYCQTO-SHAFGOBASA-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/h12,14,19-20,22-25,33H,2,6-11,13,15-17H2,1,3-5H3,(H,31,32)/t19-,20+,22-,23-,24+,25+,27+,28-,29+/m1/s1
SMILES:	CC[C@](C(=C)C)(CC[C@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]1[C@H]2CC[C@@H]2[C@]1(C)C=CC(=O)C2)C(=O)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1221624
PubChem CID:	49864372
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	=	2.4	uM	PMID[552971]

☑ 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 NPC262043 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	1002
0.2-0.3	4791
0.3-0.4	13782
0.4-0.5	8682
0.5-0.6	7005
0.6-0.7	4915
0.7-0.8	1978
0.8-0.85	301
0.85-0.9	62
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9759	High Similarity	NPC136948
0.9535	High Similarity	NPC204341
0.9518	High Similarity	NPC29447
0.9186	High Similarity	NPC117122
0.9176	High Similarity	NPC472869
0.9167	High Similarity	NPC164577
0.9157	High Similarity	NPC320514
0.907	High Similarity	NPC236618
0.9059	High Similarity	NPC269638
0.9048	High Similarity	NPC97913
0.9036	High Similarity	NPC477372
0.9036	High Similarity	NPC278459
0.9036	High Similarity	NPC147066
0.9	High Similarity	NPC171395
0.8966	High Similarity	NPC472870
0.8953	High Similarity	NPC186975
0.8941	High Similarity	NPC19849
0.8941	High Similarity	NPC472865
0.8941	High Similarity	NPC472864
0.8929	High Similarity	NPC472239
0.8876	High Similarity	NPC474018
0.8876	High Similarity	NPC473986
0.8864	High Similarity	NPC66344
0.8851	High Similarity	NPC128644
0.8851	High Similarity	NPC476409
0.8824	High Similarity	NPC470015
0.8824	High Similarity	NPC168188
0.8824	High Similarity	NPC477373
0.881	High Similarity	NPC38350
0.881	High Similarity	NPC201912
0.8795	High Similarity	NPC477371
0.8791	High Similarity	NPC476174
0.8764	High Similarity	NPC472866
0.875	High Similarity	NPC48107
0.8721	High Similarity	NPC248758
0.8706	High Similarity	NPC133391
0.8706	High Similarity	NPC260956
0.8706	High Similarity	NPC100297
0.8706	High Similarity	NPC472867
0.8706	High Similarity	NPC142253
0.8706	High Similarity	NPC3511
0.8706	High Similarity	NPC193347
0.8696	High Similarity	NPC472941
0.8696	High Similarity	NPC456
0.8696	High Similarity	NPC29152
0.8681	High Similarity	NPC8993
0.8675	High Similarity	NPC275494
0.8675	High Similarity	NPC179028
0.8675	High Similarity	NPC471409
0.8667	High Similarity	NPC475806
0.8636	High Similarity	NPC96496
0.8636	High Similarity	NPC93778
0.8621	High Similarity	NPC474537
0.8621	High Similarity	NPC311702
0.8621	High Similarity	NPC123319
0.8621	High Similarity	NPC8571
0.8621	High Similarity	NPC94531
0.8621	High Similarity	NPC60350
0.8605	High Similarity	NPC83569
0.8605	High Similarity	NPC472740
0.8605	High Similarity	NPC3856
0.8605	High Similarity	NPC69279
0.8605	High Similarity	NPC279639
0.8605	High Similarity	NPC477852
0.8605	High Similarity	NPC310470
0.8605	High Similarity	NPC167103
0.8605	High Similarity	NPC49019
0.8602	High Similarity	NPC108078
0.8602	High Similarity	NPC107243
0.8602	High Similarity	NPC156546
0.8588	High Similarity	NPC471898
0.8571	High Similarity	NPC474807
0.8571	High Similarity	NPC472871
0.8571	High Similarity	NPC215843
0.8571	High Similarity	NPC474736
0.8554	High Similarity	NPC97377
0.8554	High Similarity	NPC165711
0.8539	High Similarity	NPC72397
0.8511	High Similarity	NPC166745
0.8511	High Similarity	NPC235464
0.8511	High Similarity	NPC197386
0.8506	High Similarity	NPC178025
0.8506	High Similarity	NPC85774
0.8506	High Similarity	NPC87552
0.8506	High Similarity	NPC96095
0.8506	High Similarity	NPC214043
0.8506	High Similarity	NPC144258
0.8506	High Similarity	NPC16287
0.8506	High Similarity	NPC165064
0.8506	High Similarity	NPC181743
0.8495	Intermediate Similarity	NPC301534
0.8495	Intermediate Similarity	NPC250757
0.8488	Intermediate Similarity	NPC469805
0.8488	Intermediate Similarity	NPC469806
0.8488	Intermediate Similarity	NPC469804
0.8488	Intermediate Similarity	NPC469799
0.8488	Intermediate Similarity	NPC302661
0.8488	Intermediate Similarity	NPC238991
0.8471	Intermediate Similarity	NPC476809
0.8471	Intermediate Similarity	NPC37038
0.8462	Intermediate Similarity	NPC476187
0.8462	Intermediate Similarity	NPC470113
0.8462	Intermediate Similarity	NPC473998
0.8452	Intermediate Similarity	NPC74410
0.8452	Intermediate Similarity	NPC198240
0.8444	Intermediate Similarity	NPC305039
0.8444	Intermediate Similarity	NPC474570
0.8444	Intermediate Similarity	NPC214387
0.8444	Intermediate Similarity	NPC309603
0.8444	Intermediate Similarity	NPC2983
0.8444	Intermediate Similarity	NPC473999
0.8434	Intermediate Similarity	NPC180886
0.8427	Intermediate Similarity	NPC476293
0.8427	Intermediate Similarity	NPC58063
0.8421	Intermediate Similarity	NPC287833
0.8409	Intermediate Similarity	NPC473038
0.8409	Intermediate Similarity	NPC142649
0.8409	Intermediate Similarity	NPC11711
0.8409	Intermediate Similarity	NPC469948
0.8409	Intermediate Similarity	NPC471224
0.8404	Intermediate Similarity	NPC253826
0.8404	Intermediate Similarity	NPC57416
0.8404	Intermediate Similarity	NPC476253
0.8391	Intermediate Similarity	NPC105803
0.8387	Intermediate Similarity	NPC173875
0.8387	Intermediate Similarity	NPC318282
0.8387	Intermediate Similarity	NPC293052
0.8387	Intermediate Similarity	NPC469995
0.8387	Intermediate Similarity	NPC174948
0.837	Intermediate Similarity	NPC243866
0.837	Intermediate Similarity	NPC476416
0.8353	Intermediate Similarity	NPC231431
0.8353	Intermediate Similarity	NPC158846
0.8352	Intermediate Similarity	NPC476369
0.8352	Intermediate Similarity	NPC477147
0.8352	Intermediate Similarity	NPC477149
0.8352	Intermediate Similarity	NPC476437
0.8352	Intermediate Similarity	NPC48010
0.8352	Intermediate Similarity	NPC320026
0.8352	Intermediate Similarity	NPC469400
0.8333	Intermediate Similarity	NPC472924
0.8333	Intermediate Similarity	NPC212661
0.8333	Intermediate Similarity	NPC471035
0.8333	Intermediate Similarity	NPC61952
0.8333	Intermediate Similarity	NPC66105
0.8333	Intermediate Similarity	NPC282524
0.8333	Intermediate Similarity	NPC224720
0.8333	Intermediate Similarity	NPC476240
0.8333	Intermediate Similarity	NPC99411
0.8333	Intermediate Similarity	NPC476223
0.8316	Intermediate Similarity	NPC114274
0.8316	Intermediate Similarity	NPC98868
0.8315	Intermediate Similarity	NPC145879
0.8315	Intermediate Similarity	NPC31564
0.8315	Intermediate Similarity	NPC469994
0.8315	Intermediate Similarity	NPC472479
0.8315	Intermediate Similarity	NPC155011
0.8315	Intermediate Similarity	NPC474733
0.8315	Intermediate Similarity	NPC474732
0.8315	Intermediate Similarity	NPC474778
0.8313	Intermediate Similarity	NPC476795
0.8313	Intermediate Similarity	NPC279666
0.8313	Intermediate Similarity	NPC192540
0.8298	Intermediate Similarity	NPC155676
0.8298	Intermediate Similarity	NPC328371
0.8298	Intermediate Similarity	NPC249954
0.8295	Intermediate Similarity	NPC476412
0.8295	Intermediate Similarity	NPC237712
0.8295	Intermediate Similarity	NPC473246
0.8295	Intermediate Similarity	NPC476038
0.8295	Intermediate Similarity	NPC209882
0.8295	Intermediate Similarity	NPC194937
0.8283	Intermediate Similarity	NPC475294
0.828	Intermediate Similarity	NPC299100
0.8276	Intermediate Similarity	NPC321289
0.8276	Intermediate Similarity	NPC327969
0.8265	Intermediate Similarity	NPC472868
0.8261	Intermediate Similarity	NPC272746
0.8261	Intermediate Similarity	NPC154101
0.8261	Intermediate Similarity	NPC218301
0.8256	Intermediate Similarity	NPC469797
0.8256	Intermediate Similarity	NPC469798
0.8256	Intermediate Similarity	NPC472478
0.8247	Intermediate Similarity	NPC293753
0.8247	Intermediate Similarity	NPC87351
0.8242	Intermediate Similarity	NPC474704
0.8242	Intermediate Similarity	NPC310236
0.8242	Intermediate Similarity	NPC118011
0.8242	Intermediate Similarity	NPC146554
0.8242	Intermediate Similarity	NPC31985
0.8242	Intermediate Similarity	NPC1015
0.8242	Intermediate Similarity	NPC472240
0.8242	Intermediate Similarity	NPC326627
0.8242	Intermediate Similarity	NPC262858
0.8242	Intermediate Similarity	NPC285982
0.8242	Intermediate Similarity	NPC476733
0.8242	Intermediate Similarity	NPC477973
0.8242	Intermediate Similarity	NPC310010
0.8242	Intermediate Similarity	NPC477943
0.8242	Intermediate Similarity	NPC215029

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 NPC262043 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1274
0.2-0.3	3856
0.3-0.4	2614
0.4-0.5	752
0.5-0.6	185
0.6-0.7	131
0.7-0.8	127
0.8-0.85	57
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8706	High Similarity	NPD4223	Phase 3
0.8706	High Similarity	NPD4221	Approved
0.8667	High Similarity	NPD5284	Approved
0.8667	High Similarity	NPD5281	Approved
0.8621	High Similarity	NPD5329	Approved
0.8523	High Similarity	NPD5690	Phase 2
0.8506	High Similarity	NPD4197	Approved
0.8444	Intermediate Similarity	NPD6904	Approved
0.8444	Intermediate Similarity	NPD6673	Approved
0.8444	Intermediate Similarity	NPD6080	Approved
0.8404	Intermediate Similarity	NPD6084	Phase 2
0.8404	Intermediate Similarity	NPD6083	Phase 2
0.8353	Intermediate Similarity	NPD4195	Approved
0.8333	Intermediate Similarity	NPD5737	Approved
0.8333	Intermediate Similarity	NPD6672	Approved
0.8315	Intermediate Similarity	NPD4623	Approved
0.8315	Intermediate Similarity	NPD4138	Approved
0.8315	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8315	Intermediate Similarity	NPD4519	Discontinued
0.8315	Intermediate Similarity	NPD5205	Approved
0.8315	Intermediate Similarity	NPD4693	Phase 3
0.8315	Intermediate Similarity	NPD4690	Approved
0.8315	Intermediate Similarity	NPD4688	Approved
0.8315	Intermediate Similarity	NPD4689	Approved
0.8261	Intermediate Similarity	NPD5693	Phase 1
0.8261	Intermediate Similarity	NPD6079	Approved
0.8242	Intermediate Similarity	NPD4753	Phase 2
0.8191	Intermediate Similarity	NPD5695	Phase 3
0.8191	Intermediate Similarity	NPD5210	Approved
0.8191	Intermediate Similarity	NPD4629	Approved
0.8172	Intermediate Similarity	NPD6399	Phase 3
0.8132	Intermediate Similarity	NPD5208	Approved
0.8125	Intermediate Similarity	NPD5696	Approved
0.8111	Intermediate Similarity	NPD5280	Approved
0.8111	Intermediate Similarity	NPD7334	Approved
0.8111	Intermediate Similarity	NPD6098	Approved
0.8111	Intermediate Similarity	NPD4694	Approved
0.8111	Intermediate Similarity	NPD6684	Approved
0.8111	Intermediate Similarity	NPD7521	Approved
0.8111	Intermediate Similarity	NPD6409	Approved
0.8111	Intermediate Similarity	NPD7146	Approved
0.8111	Intermediate Similarity	NPD5330	Approved
0.809	Intermediate Similarity	NPD3666	Approved
0.809	Intermediate Similarity	NPD3133	Approved
0.809	Intermediate Similarity	NPD4786	Approved
0.809	Intermediate Similarity	NPD3665	Phase 1
0.8065	Intermediate Similarity	NPD5694	Approved
0.8065	Intermediate Similarity	NPD6050	Approved
0.8061	Intermediate Similarity	NPD5211	Phase 2
0.8046	Intermediate Similarity	NPD4695	Discontinued
0.8043	Intermediate Similarity	NPD5328	Approved
0.8023	Intermediate Similarity	NPD3617	Approved
0.802	Intermediate Similarity	NPD6881	Approved
0.802	Intermediate Similarity	NPD6899	Approved
0.8	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD5207	Approved
0.7957	Intermediate Similarity	NPD5692	Phase 3
0.7935	Intermediate Similarity	NPD6903	Approved
0.7935	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD5697	Approved
0.7917	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD5221	Approved
0.7917	Intermediate Similarity	NPD5222	Approved
0.7912	Intermediate Similarity	NPD3618	Phase 1
0.79	Intermediate Similarity	NPD5141	Approved
0.7872	Intermediate Similarity	NPD7515	Phase 2
0.7865	Intermediate Similarity	NPD3667	Approved
0.7864	Intermediate Similarity	NPD7102	Approved
0.7864	Intermediate Similarity	NPD7290	Approved
0.7864	Intermediate Similarity	NPD6883	Approved
0.7857	Intermediate Similarity	NPD6404	Discontinued
0.7857	Intermediate Similarity	NPD5285	Approved
0.7857	Intermediate Similarity	NPD5286	Approved
0.7857	Intermediate Similarity	NPD4696	Approved
0.7849	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD6011	Approved
0.7835	Intermediate Similarity	NPD5173	Approved
0.7831	Intermediate Similarity	NPD4747	Approved
0.7831	Intermediate Similarity	NPD4691	Approved
0.7826	Intermediate Similarity	NPD3573	Approved
0.7822	Intermediate Similarity	NPD6675	Approved
0.7822	Intermediate Similarity	NPD6402	Approved
0.7822	Intermediate Similarity	NPD7128	Approved
0.7822	Intermediate Similarity	NPD5739	Approved
0.7789	Intermediate Similarity	NPD4202	Approved
0.7788	Intermediate Similarity	NPD6617	Approved
0.7788	Intermediate Similarity	NPD6869	Approved
0.7788	Intermediate Similarity	NPD8130	Phase 1
0.7788	Intermediate Similarity	NPD6847	Approved
0.7788	Intermediate Similarity	NPD6650	Approved
0.7788	Intermediate Similarity	NPD6649	Approved
0.7778	Intermediate Similarity	NPD4788	Approved
0.7778	Intermediate Similarity	NPD5223	Approved
0.7767	Intermediate Similarity	NPD6012	Approved
0.7767	Intermediate Similarity	NPD6014	Approved
0.7767	Intermediate Similarity	NPD6013	Approved
0.7765	Intermediate Similarity	NPD4058	Approved
0.7757	Intermediate Similarity	NPD7115	Discovery
0.7717	Intermediate Similarity	NPD5279	Phase 3
0.7714	Intermediate Similarity	NPD6882	Approved
0.7714	Intermediate Similarity	NPD8297	Approved
0.7711	Intermediate Similarity	NPD4137	Phase 3
0.7708	Intermediate Similarity	NPD7748	Approved
0.7708	Intermediate Similarity	NPD6001	Approved
0.77	Intermediate Similarity	NPD5225	Approved
0.77	Intermediate Similarity	NPD5091	Approved
0.77	Intermediate Similarity	NPD4633	Approved
0.77	Intermediate Similarity	NPD5226	Approved
0.77	Intermediate Similarity	NPD5224	Approved
0.767	Intermediate Similarity	NPD7320	Approved
0.7653	Intermediate Similarity	NPD4755	Approved
0.7624	Intermediate Similarity	NPD5175	Approved
0.7624	Intermediate Similarity	NPD5174	Approved
0.7614	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD6373	Approved
0.7596	Intermediate Similarity	NPD6372	Approved
0.7579	Intermediate Similarity	NPD4096	Approved
0.7573	Intermediate Similarity	NPD6614	Approved
0.7573	Intermediate Similarity	NPD5701	Approved
0.7558	Intermediate Similarity	NPD4785	Approved
0.7558	Intermediate Similarity	NPD4784	Approved
0.7558	Intermediate Similarity	NPD4687	Approved
0.7558	Intermediate Similarity	NPD5733	Approved
0.7556	Intermediate Similarity	NPD4139	Approved
0.7556	Intermediate Similarity	NPD4692	Approved
0.7553	Intermediate Similarity	NPD4518	Approved
0.7551	Intermediate Similarity	NPD7614	Phase 1
0.7551	Intermediate Similarity	NPD4697	Phase 3
0.7529	Intermediate Similarity	NPD4243	Approved
0.75	Intermediate Similarity	NPD3668	Phase 3
0.75	Intermediate Similarity	NPD4700	Approved
0.75	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.7477	Intermediate Similarity	NPD4632	Approved
0.7475	Intermediate Similarity	NPD7902	Approved
0.7473	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6052	Approved
0.7449	Intermediate Similarity	NPD5654	Approved
0.7423	Intermediate Similarity	NPD5133	Approved
0.7419	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7638	Approved
0.7364	Intermediate Similarity	NPD6335	Approved
0.7339	Intermediate Similarity	NPD6868	Approved
0.7333	Intermediate Similarity	NPD4730	Approved
0.7333	Intermediate Similarity	NPD4729	Approved
0.7326	Intermediate Similarity	NPD5276	Approved
0.7326	Intermediate Similarity	NPD6081	Approved
0.73	Intermediate Similarity	NPD5959	Approved
0.7297	Intermediate Similarity	NPD7100	Approved
0.7297	Intermediate Similarity	NPD7101	Approved
0.7282	Intermediate Similarity	NPD4754	Approved
0.7273	Intermediate Similarity	NPD6317	Approved
0.7273	Intermediate Similarity	NPD6009	Approved
0.7234	Intermediate Similarity	NPD5363	Approved
0.7216	Intermediate Similarity	NPD5785	Approved
0.7207	Intermediate Similarity	NPD6313	Approved
0.7207	Intermediate Similarity	NPD6314	Approved
0.7196	Intermediate Similarity	NPD5248	Approved
0.7196	Intermediate Similarity	NPD5249	Phase 3
0.7196	Intermediate Similarity	NPD5247	Approved
0.7196	Intermediate Similarity	NPD5135	Approved
0.7196	Intermediate Similarity	NPD5250	Approved
0.7196	Intermediate Similarity	NPD5251	Approved
0.7196	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4634	Approved
0.7196	Intermediate Similarity	NPD5169	Approved
0.7182	Intermediate Similarity	NPD6274	Approved
0.7176	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7900	Approved
0.717	Intermediate Similarity	NPD5128	Approved
0.717	Intermediate Similarity	NPD5168	Approved
0.7143	Intermediate Similarity	NPD4224	Phase 2
0.7143	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD8034	Phase 2
0.7143	Intermediate Similarity	NPD4767	Approved
0.7143	Intermediate Similarity	NPD4768	Approved
0.7143	Intermediate Similarity	NPD8035	Phase 2
0.713	Intermediate Similarity	NPD5217	Approved
0.713	Intermediate Similarity	NPD5216	Approved
0.713	Intermediate Similarity	NPD5127	Approved
0.713	Intermediate Similarity	NPD5215	Approved
0.7113	Intermediate Similarity	NPD6051	Approved
0.708	Intermediate Similarity	NPD6319	Approved
0.7079	Intermediate Similarity	NPD6942	Approved
0.7079	Intermediate Similarity	NPD4190	Phase 3
0.7079	Intermediate Similarity	NPD5275	Approved
0.7079	Intermediate Similarity	NPD7339	Approved
0.7075	Intermediate Similarity	NPD6412	Phase 2
0.7065	Intermediate Similarity	NPD7525	Registered
0.7053	Intermediate Similarity	NPD1694	Approved
0.7043	Intermediate Similarity	NPD7604	Phase 2
0.703	Intermediate Similarity	NPD7732	Phase 3
0.7021	Intermediate Similarity	NPD5362	Discontinued
0.7018	Intermediate Similarity	NPD5983	Phase 2
0.7018	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7492	Approved
0.6977	Remote Similarity	NPD5360	Phase 3
0.6977	Remote Similarity	NPD5361	Clinical (unspecified phase)

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