NPASS Compound

Structure

NPC474531 OpenBabel07101719132D 30 33 0 0 1 0 0 0 0 0999 V2000 6.6294 7.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9821 7.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7023 4.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0574 3.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3422 6.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3641 5.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6512 7.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7242 4.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.0550 5.0032 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0769 4.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 6 11 1 0 0 0 0 6 16 2 0 0 0 0 7 8 1 0 0 0 0 7 18 2 0 0 0 0 8 22 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 17 3 1 1 0 0 0 17 19 1 0 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 26 1 1 0 0 0 20 26 1 1 0 0 0 21 27 1 1 0 0 0 22 25 1 0 0 0 0 22 27 1 0 0 0 0 23 28 1 6 0 0 0 24 25 1 0 0 0 0 24 29 1 1 0 0 0 25 30 1 1 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.33
Volume:	462.42
LogP:	5.316
LogD:	5.001
LogS:	-5.318
# Rotatable Bonds:	4
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.549
Synthetic Accessibility Score:	4.883
Fsp3:	0.852
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.82
MDCK Permeability:	4.489942148211412e-05
Pgp-inhibitor:	0.38
Pgp-substrate:	0.715
Human Intestinal Absorption (HIA):	0.062
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	92.52375030517578%
Volume Distribution (VD):	1.075
Pgp-substrate:	2.6285390853881836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.107
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.713
CYP2C9-inhibitor:	0.12
CYP2C9-substrate:	0.814
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.237
CYP3A4-inhibitor:	0.6
CYP3A4-substrate:	0.145

ADMET: Excretion

Clearance (CL):	4.987
Half-life (T1/2):	0.108

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.268
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.034
Skin Sensitization:	0.263
Carcinogencity:	0.009
Eye Corrosion:	0.015
Eye Irritation:	0.344
Respiratory Toxicity:	0.674

Download Data

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

Natural Product: NPC474531

Natural Product ID:	NPC474531
*Common Name:**	(3S,4R,22R)-Cholest-7,24-Diene-3,4,22-Triol
IUPAC Name:	(3S,4R,9R,10R,13R,14R,17R)-17-[(2S,3R)-3-hydroxy-6-methylhept-5-en-2-yl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,4-diol
Synonyms:
Standard InCHIKey:	JGBRCVYPUYKCSI-LCKPLGNHSA-N
Standard InCHI:	InChI=1S/C27H44O3/c1-16(2)6-11-23(28)17(3)19-9-10-20-18-7-8-22-25(30)24(29)13-15-27(22,5)21(18)12-14-26(19,20)4/h6-7,17,19-25,28-30H,8-15H2,1-5H3/t17-,19+,20-,21-,22?,23+,24-,25+,26+,27+/m0/s1
SMILES:	CC(C1CCC2C1(CCC3C2=CCC4C3(CCC(C4O)O)C)C)C(CC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471175
PubChem CID:	44575585
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0001104] Trihydroxy bile acids, alcohols 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
NPO3427	Aglaia rubiginosa	Species	Meliaceae	Eukaryota	twigs and leaves	n.a.	n.a.	PMID[15043407]
NPO3427	Aglaia rubiginosa	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
EC50	1
ED50	5

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	1.0	10'3nM	PMID[506504]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	1.0	10'3nM	PMID[506504]
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	>	1.0	10'3nM	PMID[506504]
NPT1851	Cell Line	Col2	Homo sapiens	EC50	>	1000.0	nM	PMID[506504]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	1.0	10'3nM	PMID[506504]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	1.0	10'3nM	PMID[506504]

☑ 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 NPC474531 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	157
0.1-0.2	1368
0.2-0.3	6021
0.3-0.4	15996
0.4-0.5	7693
0.5-0.6	5263
0.6-0.7	4419
0.7-0.8	1341
0.8-0.85	254
0.85-0.9	132
0.9-0.95	50
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9867	High Similarity	NPC236112
0.9487	High Similarity	NPC317458
0.9474	High Similarity	NPC328714
0.9375	High Similarity	NPC94462
0.9359	High Similarity	NPC30166
0.9351	High Similarity	NPC13554
0.9342	High Similarity	NPC275910
0.9333	High Similarity	NPC300324
0.9333	High Similarity	NPC107059
0.9333	High Similarity	NPC240604
0.9333	High Similarity	NPC321381
0.9333	High Similarity	NPC321016
0.9333	High Similarity	NPC189883
0.9241	High Similarity	NPC207013
0.9221	High Similarity	NPC1319
0.9211	High Similarity	NPC198968
0.9211	High Similarity	NPC214570
0.9211	High Similarity	NPC155986
0.9211	High Similarity	NPC318495
0.92	High Similarity	NPC141071
0.92	High Similarity	NPC471723
0.92	High Similarity	NPC477923
0.92	High Similarity	NPC288035
0.92	High Similarity	NPC257347
0.92	High Similarity	NPC66566
0.92	High Similarity	NPC134847
0.92	High Similarity	NPC285893
0.92	High Similarity	NPC28657
0.92	High Similarity	NPC136188
0.92	High Similarity	NPC304309
0.92	High Similarity	NPC22105
0.92	High Similarity	NPC230301
0.92	High Similarity	NPC162742
0.9136	High Similarity	NPC477604
0.9125	High Similarity	NPC185568
0.9103	High Similarity	NPC22403
0.9091	High Similarity	NPC477522
0.9091	High Similarity	NPC138621
0.9091	High Similarity	NPC87604
0.9091	High Similarity	NPC6978
0.9091	High Similarity	NPC167037
0.9091	High Similarity	NPC473943
0.9091	High Similarity	NPC285761
0.9091	High Similarity	NPC474216
0.9091	High Similarity	NPC244385
0.9079	High Similarity	NPC73875
0.9079	High Similarity	NPC134330
0.9079	High Similarity	NPC129165
0.9079	High Similarity	NPC202642
0.9079	High Similarity	NPC113733
0.9079	High Similarity	NPC46160
0.9079	High Similarity	NPC237460
0.9036	High Similarity	NPC105495
0.9	High Similarity	NPC474634
0.8987	High Similarity	NPC470383
0.8987	High Similarity	NPC6707
0.8974	High Similarity	NPC30986
0.8974	High Similarity	NPC209430
0.8974	High Similarity	NPC84694
0.8974	High Similarity	NPC109546
0.8974	High Similarity	NPC273410
0.8974	High Similarity	NPC81306
0.8974	High Similarity	NPC28862
0.8974	High Similarity	NPC143182
0.8974	High Similarity	NPC47982
0.8974	High Similarity	NPC80530
0.8961	High Similarity	NPC477924
0.8961	High Similarity	NPC34019
0.8947	High Similarity	NPC118508
0.8947	High Similarity	NPC121744
0.8947	High Similarity	NPC322353
0.8916	High Similarity	NPC474668
0.8916	High Similarity	NPC133588
0.8902	High Similarity	NPC269058
0.8902	High Similarity	NPC125399
0.8902	High Similarity	NPC71520
0.8889	High Similarity	NPC124172
0.8889	High Similarity	NPC209802
0.8875	High Similarity	NPC248886
0.8875	High Similarity	NPC201852
0.8875	High Similarity	NPC101462
0.8875	High Similarity	NPC49964
0.8875	High Similarity	NPC7988
0.8875	High Similarity	NPC470049
0.8861	High Similarity	NPC102253
0.8861	High Similarity	NPC26117
0.8861	High Similarity	NPC287749
0.8861	High Similarity	NPC236237
0.8861	High Similarity	NPC164840
0.8861	High Similarity	NPC234193
0.8861	High Similarity	NPC209944
0.8861	High Similarity	NPC241290
0.8861	High Similarity	NPC322313
0.8846	High Similarity	NPC102708
0.8846	High Similarity	NPC85346
0.8846	High Similarity	NPC186191
0.8846	High Similarity	NPC18603
0.8846	High Similarity	NPC302041
0.8846	High Similarity	NPC307965
0.8846	High Similarity	NPC205455
0.8846	High Similarity	NPC65897
0.8846	High Similarity	NPC76931
0.8831	High Similarity	NPC470362
0.8831	High Similarity	NPC91573
0.8831	High Similarity	NPC477925
0.8831	High Similarity	NPC274079
0.8831	High Similarity	NPC96319
0.8816	High Similarity	NPC243342
0.8816	High Similarity	NPC477138
0.881	High Similarity	NPC470361
0.881	High Similarity	NPC477606
0.8795	High Similarity	NPC470620
0.875	High Similarity	NPC474752
0.875	High Similarity	NPC82986
0.875	High Similarity	NPC474759
0.875	High Similarity	NPC474731
0.875	High Similarity	NPC474683
0.875	High Similarity	NPC47761
0.875	High Similarity	NPC264245
0.875	High Similarity	NPC7505
0.875	High Similarity	NPC23852
0.875	High Similarity	NPC209620
0.875	High Similarity	NPC70927
0.8734	High Similarity	NPC472463
0.8718	High Similarity	NPC130136
0.8718	High Similarity	NPC471798
0.8706	High Similarity	NPC204188
0.8706	High Similarity	NPC80561
0.8706	High Similarity	NPC329596
0.8706	High Similarity	NPC3345
0.8706	High Similarity	NPC291484
0.8706	High Similarity	NPC11216
0.8701	High Similarity	NPC291503
0.869	High Similarity	NPC67872
0.869	High Similarity	NPC475664
0.8684	High Similarity	NPC474140
0.8684	High Similarity	NPC471799
0.8684	High Similarity	NPC201373
0.8684	High Similarity	NPC182717
0.8675	High Similarity	NPC24277
0.8675	High Similarity	NPC474970
0.8675	High Similarity	NPC6391
0.8675	High Similarity	NPC261266
0.8659	High Similarity	NPC478102
0.8659	High Similarity	NPC205845
0.8659	High Similarity	NPC470077
0.8659	High Similarity	NPC238992
0.8642	High Similarity	NPC1272
0.8642	High Similarity	NPC296701
0.8642	High Similarity	NPC47763
0.8642	High Similarity	NPC20853
0.8642	High Similarity	NPC87489
0.8642	High Similarity	NPC50964
0.8642	High Similarity	NPC202389
0.8642	High Similarity	NPC189972
0.8642	High Similarity	NPC470614
0.8642	High Similarity	NPC5985
0.8642	High Similarity	NPC218616
0.8608	High Similarity	NPC474989
0.8608	High Similarity	NPC83351
0.8608	High Similarity	NPC22955
0.8608	High Similarity	NPC167891
0.8608	High Similarity	NPC312328
0.8608	High Similarity	NPC318136
0.8608	High Similarity	NPC99168
0.8608	High Similarity	NPC477514
0.8608	High Similarity	NPC470396
0.8605	High Similarity	NPC41554
0.8605	High Similarity	NPC97404
0.8605	High Similarity	NPC189520
0.859	High Similarity	NPC244488
0.859	High Similarity	NPC247325
0.859	High Similarity	NPC315261
0.8588	High Similarity	NPC32830
0.8571	High Similarity	NPC469593
0.8571	High Similarity	NPC474657
0.8571	High Similarity	NPC469534
0.8571	High Similarity	NPC91858
0.8571	High Similarity	NPC469533
0.8571	High Similarity	NPC471797
0.8571	High Similarity	NPC186145
0.8571	High Similarity	NPC100334
0.8554	High Similarity	NPC266511
0.8554	High Similarity	NPC318390
0.8554	High Similarity	NPC274448
0.8554	High Similarity	NPC157257
0.8553	High Similarity	NPC242001
0.8553	High Similarity	NPC111234
0.8553	High Similarity	NPC167706
0.8553	High Similarity	NPC242992
0.8537	High Similarity	NPC253402
0.8537	High Similarity	NPC159168
0.8537	High Similarity	NPC475789
0.8537	High Similarity	NPC110778
0.8537	High Similarity	NPC113978
0.8537	High Similarity	NPC477818
0.8519	High Similarity	NPC473534
0.85	High Similarity	NPC291379
0.85	High Similarity	NPC53744
0.8488	Intermediate Similarity	NPC473956

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 NPC474531 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1617
0.2-0.3	4401
0.3-0.4	2110
0.4-0.5	443
0.5-0.6	155
0.6-0.7	173
0.7-0.8	71
0.8-0.85	18
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.92	High Similarity	NPD6942	Approved
0.92	High Similarity	NPD7339	Approved
0.8861	High Similarity	NPD7525	Registered
0.8831	High Similarity	NPD3701	Clinical (unspecified phase)
0.859	High Similarity	NPD6933	Approved
0.8434	Intermediate Similarity	NPD4786	Approved
0.8333	Intermediate Similarity	NPD6924	Approved
0.8333	Intermediate Similarity	NPD6926	Approved
0.8272	Intermediate Similarity	NPD7645	Phase 2
0.8193	Intermediate Similarity	NPD3667	Approved
0.8161	Intermediate Similarity	NPD5328	Approved
0.8101	Intermediate Similarity	NPD4784	Approved
0.8101	Intermediate Similarity	NPD4785	Approved
0.8077	Intermediate Similarity	NPD7150	Approved
0.8077	Intermediate Similarity	NPD4243	Approved
0.8077	Intermediate Similarity	NPD7152	Approved
0.8077	Intermediate Similarity	NPD7151	Approved
0.8052	Intermediate Similarity	NPD6923	Approved
0.8052	Intermediate Similarity	NPD6922	Approved
0.8023	Intermediate Similarity	NPD3618	Phase 1
0.7978	Intermediate Similarity	NPD6079	Approved
0.7952	Intermediate Similarity	NPD4748	Discontinued
0.7949	Intermediate Similarity	NPD7144	Approved
0.7949	Intermediate Similarity	NPD7143	Approved
0.7931	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6929	Approved
0.7738	Intermediate Similarity	NPD6931	Approved
0.7738	Intermediate Similarity	NPD6930	Phase 2
0.7738	Intermediate Similarity	NPD7509	Discontinued
0.7727	Intermediate Similarity	NPD7524	Approved
0.7692	Intermediate Similarity	NPD4202	Approved
0.7595	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5776	Phase 2
0.759	Intermediate Similarity	NPD6925	Approved
0.759	Intermediate Similarity	NPD6932	Approved
0.7586	Intermediate Similarity	NPD3665	Phase 1
0.7586	Intermediate Similarity	NPD3666	Approved
0.7586	Intermediate Similarity	NPD3133	Approved
0.7561	Intermediate Similarity	NPD4190	Phase 3
0.7561	Intermediate Similarity	NPD5275	Approved
0.75	Intermediate Similarity	NPD7145	Approved
0.75	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6399	Phase 3
0.7471	Intermediate Similarity	NPD6695	Phase 3
0.7447	Intermediate Similarity	NPD5221	Approved
0.7447	Intermediate Similarity	NPD4697	Phase 3
0.7447	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5222	Approved
0.7412	Intermediate Similarity	NPD4195	Approved
0.7412	Intermediate Similarity	NPD6683	Phase 2
0.7386	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3668	Phase 3
0.7368	Intermediate Similarity	NPD5173	Approved
0.7368	Intermediate Similarity	NPD4755	Approved
0.7349	Intermediate Similarity	NPD8264	Approved
0.7326	Intermediate Similarity	NPD7514	Phase 3
0.7303	Intermediate Similarity	NPD6893	Approved
0.7294	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6902	Approved
0.7222	Intermediate Similarity	NPD5279	Phase 3
0.7216	Intermediate Similarity	NPD5286	Approved
0.7216	Intermediate Similarity	NPD5285	Approved
0.7216	Intermediate Similarity	NPD4700	Approved
0.7216	Intermediate Similarity	NPD4696	Approved
0.7204	Intermediate Similarity	NPD7515	Phase 2
0.7174	Intermediate Similarity	NPD4753	Phase 2
0.7159	Intermediate Similarity	NPD4223	Phase 3
0.7159	Intermediate Similarity	NPD4221	Approved
0.7143	Intermediate Similarity	NPD5223	Approved
0.7143	Intermediate Similarity	NPD7750	Discontinued
0.7143	Intermediate Similarity	NPD4159	Approved
0.7126	Intermediate Similarity	NPD7332	Phase 2
0.7113	Intermediate Similarity	NPD7638	Approved
0.7113	Intermediate Similarity	NPD5290	Discontinued
0.7111	Intermediate Similarity	NPD5329	Approved
0.7071	Intermediate Similarity	NPD5211	Phase 2
0.7071	Intermediate Similarity	NPD4633	Approved
0.7071	Intermediate Similarity	NPD5225	Approved
0.7071	Intermediate Similarity	NPD5226	Approved
0.7071	Intermediate Similarity	NPD5224	Approved
0.7045	Intermediate Similarity	NPD6898	Phase 1
0.7041	Intermediate Similarity	NPD7639	Approved
0.7041	Intermediate Similarity	NPD7640	Approved
0.703	Intermediate Similarity	NPD6402	Approved
0.703	Intermediate Similarity	NPD5739	Approved
0.703	Intermediate Similarity	NPD6675	Approved
0.703	Intermediate Similarity	NPD7128	Approved
0.7	Intermediate Similarity	NPD4754	Approved
0.7	Intermediate Similarity	NPD5174	Approved
0.7	Intermediate Similarity	NPD4197	Approved
0.7	Intermediate Similarity	NPD5175	Approved
0.6931	Remote Similarity	NPD5141	Approved
0.6923	Remote Similarity	NPD4634	Approved
0.6893	Remote Similarity	NPD6899	Approved
0.6893	Remote Similarity	NPD6881	Approved
0.6893	Remote Similarity	NPD7320	Approved
0.6889	Remote Similarity	NPD4788	Approved
0.6875	Remote Similarity	NPD7748	Approved
0.6867	Remote Similarity	NPD4787	Phase 1
0.6863	Remote Similarity	NPD4767	Approved
0.6863	Remote Similarity	NPD4768	Approved
0.6852	Remote Similarity	NPD7115	Discovery
0.6848	Remote Similarity	NPD5330	Approved
0.6848	Remote Similarity	NPD5205	Approved
0.6848	Remote Similarity	NPD4138	Approved
0.6848	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7521	Approved
0.6848	Remote Similarity	NPD4689	Approved
0.6848	Remote Similarity	NPD4688	Approved
0.6848	Remote Similarity	NPD6684	Approved
0.6848	Remote Similarity	NPD4690	Approved
0.6848	Remote Similarity	NPD7146	Approved
0.6848	Remote Similarity	NPD4693	Phase 3
0.6848	Remote Similarity	NPD7334	Approved
0.6848	Remote Similarity	NPD6409	Approved
0.6842	Remote Similarity	NPD8035	Phase 2
0.6842	Remote Similarity	NPD8034	Phase 2
0.6842	Remote Similarity	NPD7087	Discontinued
0.6837	Remote Similarity	NPD6084	Phase 2
0.6837	Remote Similarity	NPD6083	Phase 2
0.6827	Remote Similarity	NPD6373	Approved
0.6827	Remote Similarity	NPD6372	Approved
0.6809	Remote Similarity	NPD6051	Approved
0.6804	Remote Similarity	NPD4629	Approved
0.6804	Remote Similarity	NPD5210	Approved
0.6796	Remote Similarity	NPD5701	Approved
0.6796	Remote Similarity	NPD5697	Approved
0.6792	Remote Similarity	NPD8297	Approved
0.6786	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4225	Approved
0.6762	Remote Similarity	NPD7102	Approved
0.6762	Remote Similarity	NPD7290	Approved
0.6762	Remote Similarity	NPD6883	Approved
0.6731	Remote Similarity	NPD5128	Approved
0.6731	Remote Similarity	NPD6011	Approved
0.6731	Remote Similarity	NPD5168	Approved
0.6731	Remote Similarity	NPD4730	Approved
0.6731	Remote Similarity	NPD4729	Approved
0.6729	Remote Similarity	NPD4632	Approved
0.6705	Remote Similarity	NPD3617	Approved
0.6702	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4723	Approved
0.6702	Remote Similarity	NPD5737	Approved
0.6702	Remote Similarity	NPD6903	Approved
0.6702	Remote Similarity	NPD4722	Approved
0.6702	Remote Similarity	NPD6672	Approved
0.6698	Remote Similarity	NPD6847	Approved
0.6698	Remote Similarity	NPD8130	Phase 1
0.6698	Remote Similarity	NPD6650	Approved
0.6698	Remote Similarity	NPD6617	Approved
0.6698	Remote Similarity	NPD6869	Approved
0.6698	Remote Similarity	NPD6649	Approved
0.6698	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD6117	Approved
0.6636	Remote Similarity	NPD6882	Approved
0.6635	Remote Similarity	NPD6412	Phase 2
0.6628	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5251	Approved
0.6604	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5250	Approved
0.6604	Remote Similarity	NPD5249	Phase 3
0.6604	Remote Similarity	NPD5247	Approved
0.6604	Remote Similarity	NPD5248	Approved
0.6604	Remote Similarity	NPD5169	Approved
0.6604	Remote Similarity	NPD5135	Approved
0.6591	Remote Similarity	NPD6116	Phase 1
0.6577	Remote Similarity	NPD7516	Approved
0.6556	Remote Similarity	NPD4695	Discontinued
0.6548	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5127	Approved
0.6542	Remote Similarity	NPD5216	Approved
0.6542	Remote Similarity	NPD5215	Approved
0.6542	Remote Similarity	NPD5217	Approved
0.6517	Remote Similarity	NPD6114	Approved
0.6517	Remote Similarity	NPD6697	Approved
0.6517	Remote Similarity	NPD6118	Approved
0.6517	Remote Similarity	NPD6115	Approved
0.65	Remote Similarity	NPD368	Approved
0.6495	Remote Similarity	NPD7637	Suspended
0.6489	Remote Similarity	NPD6098	Approved
0.6486	Remote Similarity	NPD7327	Approved
0.6486	Remote Similarity	NPD7328	Approved
0.6484	Remote Similarity	NPD4692	Approved
0.6484	Remote Similarity	NPD4139	Approved
0.6471	Remote Similarity	NPD4747	Approved
0.6465	Remote Similarity	NPD5695	Phase 3
0.6465	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.646	Remote Similarity	NPD8033	Approved
0.6455	Remote Similarity	NPD6868	Approved
0.6436	Remote Similarity	NPD5696	Approved
0.6408	Remote Similarity	NPD7632	Discontinued

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