NPASS Compound

Structure

CID30166 OpenBabel06191715352D 34 37 0 0 1 0 0 0 0 0999 V2000 -0.2730 3.2261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3803 -2.9616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2557 -2.4560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6442 2.3455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5426 3.3149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5349 0.5240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6906 -1.9509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6891 0.9746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6897 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2240 -0.4866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3795 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6888 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8446 1.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8151 2.5390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 2.4374 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8454 1.4627 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6900 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8452 -0.4876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2118 3.4293 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5355 -1.4628 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2243 -1.4623 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1812 3.5310 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3800 -1.9504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7539 2.7422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5352 -0.4871 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9751 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6391 4.2181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0905 -1.9621 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5779 4.4213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3572 1.8519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 21 2 0 0 0 0 10 23 1 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 28 1 0 0 0 0 15 30 1 0 0 0 0 16 29 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 0 0 0 0 18 1 1 6 0 0 0 18 19 1 0 0 0 0 19 29 1 1 0 0 0 20 21 1 0 0 0 0 20 28 1 6 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 6 0 0 0 23 26 1 0 0 0 0 23 28 1 6 0 0 0 24 26 1 0 0 0 0 24 32 1 6 0 0 0 25 27 1 0 0 0 0 25 33 1 1 0 0 0 27 34 1 0 0 0 0 28 6 1 6 0 0 0 29 30 1 1 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.39
Volume:	525.735
LogP:	5.271
LogD:	4.701
LogS:	-4.125
# Rotatable Bonds:	5
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	4.945
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.753
MDCK Permeability:	1.2026682270516176e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.03
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.931
30% Bioavailability (F30%):	0.199

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.327
Plasma Protein Binding (PPB):	95.5997085571289%
Volume Distribution (VD):	1.018
Pgp-substrate:	2.9736883640289307%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.158
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.07
CYP2C9-substrate:	0.086
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.522
CYP3A4-substrate:	0.451

ADMET: Excretion

Clearance (CL):	6.673
Half-life (T1/2):	0.078

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.266
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.977
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.274
Carcinogencity:	0.077
Eye Corrosion:	0.005
Eye Irritation:	0.022
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC30166

Natural Product ID:	NPC30166
*Common Name:**	Hispidol B
IUPAC Name:	(3S,4R,6S)-6-[(3S,5R,9R,10R,13S,14S,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptane-2,3,4-triol
Synonyms:
Standard InCHIKey:	MVWLZBQPRMCRKT-ZAVAKTSASA-N
Standard InCHI:	InChI=1S/C30H52O4/c1-18(17-22(31)25(33)27(4,5)34)19-11-15-30(8)21-9-10-23-26(2,3)24(32)13-14-28(23,6)20(21)12-16-29(19,30)7/h9,18-20,22-25,31-34H,10-17H2,1-8H3/t18-,19-,20-,22+,23-,24-,25-,28+,29-,30+/m0/s1
SMILES:	C[C@@H](C[C@H]([C@@H](C(C)(C)O)O)O)[C@@H]1CC[C@]2(C)C3=CC[C@H]4C(C)(C)[C@H](CC[C@]4(C)[C@H]3CC[C@@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386312
PubChem CID:	13967183
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO10033	Turraea pubescens	Species	Meliaceae	Eukaryota	twig	Dongfang, Hainan Province, China	2010-Mar	PMID[23734701]
NPO10033	Turraea pubescens	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	20000.0	nM	PMID[541421]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	10000.0	nM	PMID[541421]

☑ 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 NPC30166 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	158
0.1-0.2	1365
0.2-0.3	5994
0.3-0.4	15612
0.4-0.5	7592
0.5-0.6	5076
0.6-0.7	4791
0.7-0.8	1696
0.8-0.85	236
0.85-0.9	149
0.9-0.95	27
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9481	High Similarity	NPC236112
0.9481	High Similarity	NPC13554
0.9367	High Similarity	NPC207013
0.9359	High Similarity	NPC474531
0.9351	High Similarity	NPC328714
0.9259	High Similarity	NPC125399
0.925	High Similarity	NPC185568
0.9231	High Similarity	NPC322313
0.9231	High Similarity	NPC102253
0.9231	High Similarity	NPC236237
0.9221	High Similarity	NPC285761
0.9211	High Similarity	NPC189883
0.9125	High Similarity	NPC474634
0.9114	High Similarity	NPC6707
0.9103	High Similarity	NPC1319
0.9103	High Similarity	NPC273410
0.9103	High Similarity	NPC80530
0.9091	High Similarity	NPC477924
0.9091	High Similarity	NPC214570
0.9091	High Similarity	NPC198968
0.9091	High Similarity	NPC318495
0.9091	High Similarity	NPC155986
0.9079	High Similarity	NPC141071
0.9079	High Similarity	NPC471723
0.9079	High Similarity	NPC257347
0.9024	High Similarity	NPC6391
0.9024	High Similarity	NPC94462
0.9012	High Similarity	NPC205845
0.9	High Similarity	NPC101462
0.8987	High Similarity	NPC22403
0.8974	High Similarity	NPC6978
0.8974	High Similarity	NPC138621
0.8974	High Similarity	NPC275910
0.8974	High Similarity	NPC244385
0.8974	High Similarity	NPC167037
0.8961	High Similarity	NPC91573
0.8961	High Similarity	NPC240604
0.8961	High Similarity	NPC300324
0.8961	High Similarity	NPC321016
0.8961	High Similarity	NPC134330
0.8961	High Similarity	NPC202642
0.8961	High Similarity	NPC129165
0.8961	High Similarity	NPC237460
0.8961	High Similarity	NPC46160
0.8961	High Similarity	NPC321381
0.8961	High Similarity	NPC73875
0.8961	High Similarity	NPC107059
0.8941	High Similarity	NPC97404
0.8941	High Similarity	NPC210268
0.8941	High Similarity	NPC41554
0.8929	High Similarity	NPC470361
0.8916	High Similarity	NPC470620
0.8902	High Similarity	NPC318390
0.8889	High Similarity	NPC317458
0.8875	High Similarity	NPC70927
0.8875	High Similarity	NPC470383
0.8861	High Similarity	NPC30986
0.8861	High Similarity	NPC209430
0.8831	High Similarity	NPC230301
0.8831	High Similarity	NPC22105
0.8831	High Similarity	NPC66566
0.8831	High Similarity	NPC136188
0.8831	High Similarity	NPC322353
0.8831	High Similarity	NPC288035
0.8831	High Similarity	NPC285893
0.8831	High Similarity	NPC118508
0.8831	High Similarity	NPC134847
0.8831	High Similarity	NPC121744
0.8831	High Similarity	NPC162742
0.8831	High Similarity	NPC28657
0.8831	High Similarity	NPC304309
0.8831	High Similarity	NPC477923
0.8824	High Similarity	NPC3345
0.8824	High Similarity	NPC80561
0.8824	High Similarity	NPC329596
0.8824	High Similarity	NPC11216
0.8824	High Similarity	NPC204188
0.8824	High Similarity	NPC291484
0.881	High Similarity	NPC67872
0.881	High Similarity	NPC474668
0.881	High Similarity	NPC133588
0.8795	High Similarity	NPC261266
0.8795	High Similarity	NPC201273
0.8795	High Similarity	NPC477604
0.8795	High Similarity	NPC71520
0.8795	High Similarity	NPC269058
0.878	High Similarity	NPC478102
0.878	High Similarity	NPC124172
0.878	High Similarity	NPC470077
0.8765	High Similarity	NPC49964
0.8765	High Similarity	NPC296701
0.8765	High Similarity	NPC87489
0.8765	High Similarity	NPC470049
0.8765	High Similarity	NPC218616
0.8765	High Similarity	NPC7988
0.8765	High Similarity	NPC47763
0.875	High Similarity	NPC209944
0.875	High Similarity	NPC241290
0.875	High Similarity	NPC164840
0.8734	High Similarity	NPC186191
0.8734	High Similarity	NPC87604
0.8734	High Similarity	NPC205455
0.8734	High Similarity	NPC302041
0.8734	High Similarity	NPC473943
0.8734	High Similarity	NPC474216
0.8734	High Similarity	NPC65897
0.8734	High Similarity	NPC85346
0.8734	High Similarity	NPC477522
0.8718	High Similarity	NPC274079
0.8718	High Similarity	NPC477925
0.8718	High Similarity	NPC113733
0.8718	High Similarity	NPC470362
0.8706	High Similarity	NPC109744
0.8706	High Similarity	NPC105495
0.8706	High Similarity	NPC32830
0.8701	High Similarity	NPC91858
0.869	High Similarity	NPC186145
0.869	High Similarity	NPC149224
0.869	High Similarity	NPC474657
0.869	High Similarity	NPC90652
0.8684	High Similarity	NPC167706
0.8675	High Similarity	NPC266511
0.8675	High Similarity	NPC470360
0.8659	High Similarity	NPC113978
0.8659	High Similarity	NPC159168
0.8659	High Similarity	NPC253402
0.8659	High Similarity	NPC110778
0.8659	High Similarity	NPC132635
0.8659	High Similarity	NPC211135
0.8659	High Similarity	NPC85095
0.8659	High Similarity	NPC216420
0.8642	High Similarity	NPC264245
0.8642	High Similarity	NPC47761
0.8625	High Similarity	NPC143182
0.8625	High Similarity	NPC84694
0.8625	High Similarity	NPC81306
0.8625	High Similarity	NPC109546
0.8625	High Similarity	NPC28862
0.8625	High Similarity	NPC47982
0.8621	High Similarity	NPC98193
0.8608	High Similarity	NPC34019
0.8608	High Similarity	NPC130136
0.8605	High Similarity	NPC473956
0.8605	High Similarity	NPC475751
0.859	High Similarity	NPC3403
0.8588	High Similarity	NPC475664
0.8588	High Similarity	NPC280556
0.8588	High Similarity	NPC470417
0.8571	High Similarity	NPC474970
0.8571	High Similarity	NPC299068
0.8571	High Similarity	NPC201373
0.8571	High Similarity	NPC474140
0.8571	High Similarity	NPC24277
0.8571	High Similarity	NPC152808
0.8571	High Similarity	NPC182717
0.8571	High Similarity	NPC293287
0.8571	High Similarity	NPC6605
0.8554	High Similarity	NPC209802
0.8554	High Similarity	NPC474047
0.8554	High Similarity	NPC231310
0.8554	High Similarity	NPC238992
0.8539	High Similarity	NPC288970
0.8537	High Similarity	NPC1272
0.8537	High Similarity	NPC20853
0.8537	High Similarity	NPC202389
0.8537	High Similarity	NPC248886
0.8537	High Similarity	NPC201852
0.8537	High Similarity	NPC470614
0.8523	High Similarity	NPC65402
0.8523	High Similarity	NPC127718
0.8519	High Similarity	NPC234193
0.8519	High Similarity	NPC26117
0.8506	High Similarity	NPC189520
0.8506	High Similarity	NPC275671
0.85	High Similarity	NPC102708
0.85	High Similarity	NPC18603
0.85	High Similarity	NPC98386
0.85	High Similarity	NPC301707
0.85	High Similarity	NPC307965
0.85	High Similarity	NPC312328
0.85	High Similarity	NPC477514
0.85	High Similarity	NPC230295
0.85	High Similarity	NPC158662
0.85	High Similarity	NPC253807
0.85	High Similarity	NPC31828
0.85	High Similarity	NPC318136
0.85	High Similarity	NPC196753
0.85	High Similarity	NPC76931
0.8488	Intermediate Similarity	NPC475921
0.8488	Intermediate Similarity	NPC477606
0.8488	Intermediate Similarity	NPC474704
0.8481	Intermediate Similarity	NPC247325
0.8481	Intermediate Similarity	NPC93662
0.8481	Intermediate Similarity	NPC278091
0.8481	Intermediate Similarity	NPC244488
0.8481	Intermediate Similarity	NPC78067
0.8481	Intermediate Similarity	NPC96319
0.8481	Intermediate Similarity	NPC315261
0.8471	Intermediate Similarity	NPC475313
0.8462	Intermediate Similarity	NPC477138

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 NPC30166 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	1625
0.2-0.3	4412
0.3-0.4	2105
0.4-0.5	436
0.5-0.6	149
0.6-0.7	135
0.7-0.8	127
0.8-0.85	12
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD7525	Registered
0.8831	High Similarity	NPD6942	Approved
0.8831	High Similarity	NPD7339	Approved
0.8481	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD6933	Approved
0.8395	Intermediate Similarity	NPD7645	Phase 2
0.8228	Intermediate Similarity	NPD6926	Approved
0.8228	Intermediate Similarity	NPD6924	Approved
0.8205	Intermediate Similarity	NPD4243	Approved
0.8182	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD4786	Approved
0.8068	Intermediate Similarity	NPD5328	Approved
0.8	Intermediate Similarity	NPD4785	Approved
0.8	Intermediate Similarity	NPD4784	Approved
0.7931	Intermediate Similarity	NPD3618	Phase 1
0.7889	Intermediate Similarity	NPD6079	Approved
0.7882	Intermediate Similarity	NPD3667	Approved
0.7857	Intermediate Similarity	NPD6931	Approved
0.7857	Intermediate Similarity	NPD4748	Discontinued
0.7857	Intermediate Similarity	NPD6930	Phase 2
0.7849	Intermediate Similarity	NPD4755	Approved
0.7841	Intermediate Similarity	NPD7524	Approved
0.7841	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD4202	Approved
0.7791	Intermediate Similarity	NPD6695	Phase 3
0.775	Intermediate Similarity	NPD7152	Approved
0.775	Intermediate Similarity	NPD7150	Approved
0.775	Intermediate Similarity	NPD7151	Approved
0.7738	Intermediate Similarity	NPD6929	Approved
0.7722	Intermediate Similarity	NPD6923	Approved
0.7722	Intermediate Similarity	NPD6922	Approved
0.7711	Intermediate Similarity	NPD6932	Approved
0.7701	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD4700	Approved
0.7684	Intermediate Similarity	NPD4696	Approved
0.7684	Intermediate Similarity	NPD5286	Approved
0.7684	Intermediate Similarity	NPD5285	Approved
0.7683	Intermediate Similarity	NPD4190	Phase 3
0.7683	Intermediate Similarity	NPD5275	Approved
0.7667	Intermediate Similarity	NPD4753	Phase 2
0.7647	Intermediate Similarity	NPD7509	Discontinued
0.7625	Intermediate Similarity	NPD7143	Approved
0.7625	Intermediate Similarity	NPD7144	Approved
0.7553	Intermediate Similarity	NPD5222	Approved
0.7553	Intermediate Similarity	NPD4697	Phase 3
0.7553	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD5221	Approved
0.7529	Intermediate Similarity	NPD4195	Approved
0.7529	Intermediate Similarity	NPD6683	Phase 2
0.7526	Intermediate Similarity	NPD5224	Approved
0.7526	Intermediate Similarity	NPD5211	Phase 2
0.7526	Intermediate Similarity	NPD5225	Approved
0.7526	Intermediate Similarity	NPD5226	Approved
0.7526	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD6925	Approved
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD3666	Approved
0.75	Intermediate Similarity	NPD5776	Phase 2
0.7475	Intermediate Similarity	NPD5739	Approved
0.7475	Intermediate Similarity	NPD6675	Approved
0.7475	Intermediate Similarity	NPD7128	Approved
0.7475	Intermediate Similarity	NPD6402	Approved
0.7474	Intermediate Similarity	NPD5173	Approved
0.7449	Intermediate Similarity	NPD5175	Approved
0.7449	Intermediate Similarity	NPD5174	Approved
0.7444	Intermediate Similarity	NPD7750	Discontinued
0.7442	Intermediate Similarity	NPD7514	Phase 3
0.7423	Intermediate Similarity	NPD5223	Approved
0.7419	Intermediate Similarity	NPD6399	Phase 3
0.7416	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD6893	Approved
0.7412	Intermediate Similarity	NPD7145	Approved
0.7374	Intermediate Similarity	NPD5141	Approved
0.7353	Intermediate Similarity	NPD4634	Approved
0.7327	Intermediate Similarity	NPD7320	Approved
0.7327	Intermediate Similarity	NPD6899	Approved
0.7327	Intermediate Similarity	NPD6881	Approved
0.7312	Intermediate Similarity	NPD7515	Phase 2
0.7303	Intermediate Similarity	NPD3668	Phase 3
0.73	Intermediate Similarity	NPD4768	Approved
0.73	Intermediate Similarity	NPD4767	Approved
0.7292	Intermediate Similarity	NPD6083	Phase 2
0.7292	Intermediate Similarity	NPD6084	Phase 2
0.7273	Intermediate Similarity	NPD4754	Approved
0.7273	Intermediate Similarity	NPD4221	Approved
0.7273	Intermediate Similarity	NPD4223	Phase 3
0.7263	Intermediate Similarity	NPD5210	Approved
0.7263	Intermediate Similarity	NPD4629	Approved
0.7255	Intermediate Similarity	NPD6372	Approved
0.7255	Intermediate Similarity	NPD6373	Approved
0.7241	Intermediate Similarity	NPD7332	Phase 2
0.7228	Intermediate Similarity	NPD5701	Approved
0.7228	Intermediate Similarity	NPD5697	Approved
0.7222	Intermediate Similarity	NPD5329	Approved
0.7216	Intermediate Similarity	NPD7638	Approved
0.7212	Intermediate Similarity	NPD8297	Approved
0.7209	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7290	Approved
0.7184	Intermediate Similarity	NPD6883	Approved
0.7184	Intermediate Similarity	NPD7102	Approved
0.7159	Intermediate Similarity	NPD6898	Phase 1
0.7159	Intermediate Similarity	NPD6902	Approved
0.7157	Intermediate Similarity	NPD4729	Approved
0.7157	Intermediate Similarity	NPD5128	Approved
0.7157	Intermediate Similarity	NPD4730	Approved
0.7143	Intermediate Similarity	NPD7640	Approved
0.7143	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD5279	Phase 3
0.7143	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7087	Discontinued
0.7115	Intermediate Similarity	NPD6869	Approved
0.7115	Intermediate Similarity	NPD6649	Approved
0.7115	Intermediate Similarity	NPD6847	Approved
0.7115	Intermediate Similarity	NPD8130	Phase 1
0.7115	Intermediate Similarity	NPD6650	Approved
0.7115	Intermediate Similarity	NPD6617	Approved
0.7111	Intermediate Similarity	NPD4197	Approved
0.7103	Intermediate Similarity	NPD7115	Discovery
0.7097	Intermediate Similarity	NPD6051	Approved
0.7087	Intermediate Similarity	NPD6014	Approved
0.7087	Intermediate Similarity	NPD6012	Approved
0.7087	Intermediate Similarity	NPD6013	Approved
0.7071	Intermediate Similarity	NPD4159	Approved
0.7059	Intermediate Similarity	NPD8264	Approved
0.7048	Intermediate Similarity	NPD6882	Approved
0.7041	Intermediate Similarity	NPD5290	Discontinued
0.7019	Intermediate Similarity	NPD5249	Phase 3
0.7019	Intermediate Similarity	NPD5250	Approved
0.7019	Intermediate Similarity	NPD5251	Approved
0.7019	Intermediate Similarity	NPD5247	Approved
0.7019	Intermediate Similarity	NPD5248	Approved
0.7	Intermediate Similarity	NPD4788	Approved
0.699	Remote Similarity	NPD6011	Approved
0.6988	Remote Similarity	NPD4787	Phase 1
0.6981	Remote Similarity	NPD4632	Approved
0.6979	Remote Similarity	NPD7748	Approved
0.6957	Remote Similarity	NPD4689	Approved
0.6957	Remote Similarity	NPD4690	Approved
0.6957	Remote Similarity	NPD4688	Approved
0.6957	Remote Similarity	NPD4693	Phase 3
0.6957	Remote Similarity	NPD4138	Approved
0.6957	Remote Similarity	NPD5205	Approved
0.6952	Remote Similarity	NPD5215	Approved
0.6952	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5216	Approved
0.6952	Remote Similarity	NPD5217	Approved
0.6947	Remote Similarity	NPD8035	Phase 2
0.6947	Remote Similarity	NPD8034	Phase 2
0.6907	Remote Similarity	NPD5695	Phase 3
0.6893	Remote Similarity	NPD6412	Phase 2
0.6881	Remote Similarity	NPD7328	Approved
0.6881	Remote Similarity	NPD7327	Approved
0.6869	Remote Similarity	NPD5696	Approved
0.6869	Remote Similarity	NPD4225	Approved
0.6857	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5135	Approved
0.6857	Remote Similarity	NPD5169	Approved
0.6827	Remote Similarity	NPD5168	Approved
0.6818	Remote Similarity	NPD7516	Approved
0.6809	Remote Similarity	NPD6672	Approved
0.6809	Remote Similarity	NPD5737	Approved
0.6809	Remote Similarity	NPD4723	Approved
0.6809	Remote Similarity	NPD4722	Approved
0.6792	Remote Similarity	NPD5127	Approved
0.6782	Remote Similarity	NPD6117	Approved
0.6774	Remote Similarity	NPD5690	Phase 2
0.6774	Remote Similarity	NPD6409	Approved
0.6774	Remote Similarity	NPD6684	Approved
0.6774	Remote Similarity	NPD5330	Approved
0.6774	Remote Similarity	NPD7521	Approved
0.6774	Remote Similarity	NPD7146	Approved
0.6774	Remote Similarity	NPD7334	Approved
0.6774	Remote Similarity	NPD5280	Approved
0.6774	Remote Similarity	NPD4694	Approved
0.6768	Remote Similarity	NPD7902	Approved
0.6757	Remote Similarity	NPD6059	Approved
0.6757	Remote Similarity	NPD6319	Approved
0.6757	Remote Similarity	NPD6054	Approved
0.6757	Remote Similarity	NPD8294	Approved
0.6757	Remote Similarity	NPD8377	Approved
0.6735	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6116	Phase 1
0.6697	Remote Similarity	NPD6274	Approved
0.6696	Remote Similarity	NPD8335	Approved
0.6696	Remote Similarity	NPD7503	Approved
0.6696	Remote Similarity	NPD8033	Approved
0.6696	Remote Similarity	NPD8380	Approved
0.6696	Remote Similarity	NPD8296	Approved
0.6696	Remote Similarity	NPD8379	Approved
0.6696	Remote Similarity	NPD8378	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD7101	Approved
0.6637	Remote Similarity	NPD6370	Approved
0.6636	Remote Similarity	NPD6009	Approved
0.6632	Remote Similarity	NPD6903	Approved
0.6632	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD3617	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