NPASS Compound

Structure

NPC472739 OpenBabel07101718332D 33 37 0 0 1 0 0 0 0 0999 V2000 4.7090 0.9425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5034 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0165 0.6173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1337 -2.3500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0281 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4557 -1.7614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1051 1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7566 0.7401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4557 -0.1860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6865 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6865 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5297 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6865 0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5297 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8432 -0.4868 0.0000 C 0 0 1 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 3.4060 2.3897 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 -0.4868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 15 1 0 0 0 0 14 27 1 0 0 0 0 15 29 1 0 0 0 0 16 21 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 31 2 0 0 0 0 19 18 1 6 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 20 29 1 6 0 0 0 21 25 1 0 0 0 0 21 32 1 1 0 0 0 22 28 1 1 0 0 0 22 30 1 0 0 0 0 23 26 1 0 0 0 0 23 33 2 0 0 0 0 24 27 1 1 0 0 0 25 26 1 0 0 0 0 25 28 1 1 0 0 0 27 4 1 1 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.34
Volume:	503.115
LogP:	5.25
LogD:	4.931
LogS:	-5.192
# Rotatable Bonds:	2
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.389
Synthetic Accessibility Score:	5.094
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.118
MDCK Permeability:	1.1510351214383263e-05
Pgp-inhibitor:	0.412
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.85

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.96
Plasma Protein Binding (PPB):	92.8937759399414%
Volume Distribution (VD):	1.072
Pgp-substrate:	3.892198085784912%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.679
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.954
CYP2C9-inhibitor:	0.148
CYP2C9-substrate:	0.557
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.719
CYP3A4-inhibitor:	0.304
CYP3A4-substrate:	0.545

ADMET: Excretion

Clearance (CL):	14.312
Half-life (T1/2):	0.063

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.065
Drug-inuced Liver Injury (DILI):	0.111
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.527
Maximum Recommended Daily Dose:	0.857
Skin Sensitization:	0.077
Carcinogencity:	0.153
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC472739

Natural Product ID:	NPC472739
*Common Name:**	MJHMUTYZFNTLDJ-ZNJAMJCFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MJHMUTYZFNTLDJ-ZNJAMJCFSA-N
Standard InCHI:	InChI=1S/C30H46O3/c1-18(17-31)19-10-12-27(4)14-15-29(6)20(24(19)27)8-9-22-28(5)13-11-23(33)26(2,3)25(28)21(32)16-30(22,29)7/h17,19-22,24-25,32H,1,8-16H2,2-7H3/t19-,20+,21+,22+,24+,25-,27+,28+,29+,30+/m0/s1
SMILES:	CC1(C2C(CC3(C(C2(CCC1=O)C)CCC4C3(CCC5(C4C(CC5)C(=C)C=O)C)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581941
PubChem CID:	n.a.
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
NPO32825	cassine xylocarpa	Species	Celastraceae	Eukaryota	dried stems	Ahuachapan, El Salvado	n.a.	PMID[25927586]

☑ 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	1
Others	4

Activity Type	# Activity
Cell Line	1
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT460	Cell Line	MT2	Homo sapiens	CC50	=	10400.0	nM	PMID[565947]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	>	50.0	%	PMID[565947]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	7900.0	nM	PMID[565947]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.3	n.a.	PMID[565947]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Activity	=	5.0	%	PMID[565947]

☑ 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 NPC472739 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	197
0.1-0.2	1750
0.2-0.3	7532
0.3-0.4	15579
0.4-0.5	6330
0.5-0.6	5051
0.6-0.7	4464
0.7-0.8	1568
0.8-0.85	157
0.85-0.9	48
0.9-0.95	14
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9756	High Similarity	NPC269396
0.9756	High Similarity	NPC98236
0.9512	High Similarity	NPC474482
0.9512	High Similarity	NPC475745
0.9512	High Similarity	NPC74595
0.9512	High Similarity	NPC264665
0.939	High Similarity	NPC475726
0.939	High Similarity	NPC472743
0.939	High Similarity	NPC175410
0.9286	High Similarity	NPC472738
0.9167	High Similarity	NPC292553
0.9167	High Similarity	NPC76518
0.907	High Similarity	NPC474719
0.9048	High Similarity	NPC474233
0.9048	High Similarity	NPC146683
0.8953	High Similarity	NPC4643
0.8953	High Similarity	NPC57469
0.8941	High Similarity	NPC264317
0.8941	High Similarity	NPC294438
0.8929	High Similarity	NPC118800
0.8929	High Similarity	NPC291320
0.8929	High Similarity	NPC471036
0.8902	High Similarity	NPC201459
0.8864	High Similarity	NPC169933
0.8837	High Similarity	NPC12774
0.8837	High Similarity	NPC2783
0.8764	High Similarity	NPC272746
0.8736	High Similarity	NPC264005
0.8736	High Similarity	NPC165895
0.8736	High Similarity	NPC33768
0.8736	High Similarity	NPC153604
0.8736	High Similarity	NPC174619
0.8736	High Similarity	NPC269360
0.8721	High Similarity	NPC102292
0.8721	High Similarity	NPC471034
0.8721	High Similarity	NPC190704
0.869	High Similarity	NPC474484
0.869	High Similarity	NPC103754
0.8667	High Similarity	NPC224060
0.8667	High Similarity	NPC244356
0.8667	High Similarity	NPC59350
0.8659	High Similarity	NPC106078
0.8652	High Similarity	NPC126993
0.8652	High Similarity	NPC191684
0.8652	High Similarity	NPC85173
0.8636	High Similarity	NPC16377
0.8636	High Similarity	NPC471900
0.8571	High Similarity	NPC164999
0.8539	High Similarity	NPC57954
0.8539	High Similarity	NPC213832
0.8539	High Similarity	NPC220498
0.8523	High Similarity	NPC259009
0.8478	Intermediate Similarity	NPC29112
0.8471	Intermediate Similarity	NPC328264
0.8462	Intermediate Similarity	NPC82138
0.8462	Intermediate Similarity	NPC294263
0.8444	Intermediate Similarity	NPC46758
0.8444	Intermediate Similarity	NPC80401
0.8444	Intermediate Similarity	NPC261994
0.8444	Intermediate Similarity	NPC183283
0.8444	Intermediate Similarity	NPC470378
0.8444	Intermediate Similarity	NPC180849
0.8444	Intermediate Similarity	NPC149761
0.8434	Intermediate Similarity	NPC23884
0.8427	Intermediate Similarity	NPC193360
0.8427	Intermediate Similarity	NPC471724
0.8427	Intermediate Similarity	NPC206060
0.8427	Intermediate Similarity	NPC474677
0.8427	Intermediate Similarity	NPC4309
0.8415	Intermediate Similarity	NPC178383
0.8415	Intermediate Similarity	NPC195155
0.8415	Intermediate Similarity	NPC212879
0.8415	Intermediate Similarity	NPC97534
0.8415	Intermediate Similarity	NPC104387
0.8415	Intermediate Similarity	NPC174964
0.8415	Intermediate Similarity	NPC231256
0.8415	Intermediate Similarity	NPC240235
0.8409	Intermediate Similarity	NPC72133
0.8409	Intermediate Similarity	NPC74363
0.8409	Intermediate Similarity	NPC475862
0.8409	Intermediate Similarity	NPC34190
0.8409	Intermediate Similarity	NPC477579
0.8409	Intermediate Similarity	NPC95594
0.8409	Intermediate Similarity	NPC94755
0.8409	Intermediate Similarity	NPC471737
0.8409	Intermediate Similarity	NPC235341
0.8387	Intermediate Similarity	NPC135548
0.8387	Intermediate Similarity	NPC264979
0.8372	Intermediate Similarity	NPC110780
0.8372	Intermediate Similarity	NPC477858
0.8372	Intermediate Similarity	NPC145143
0.837	Intermediate Similarity	NPC303863
0.8352	Intermediate Similarity	NPC476168
0.8352	Intermediate Similarity	NPC160506
0.8352	Intermediate Similarity	NPC475416
0.8352	Intermediate Similarity	NPC299185
0.8333	Intermediate Similarity	NPC122116
0.8333	Intermediate Similarity	NPC271974
0.8333	Intermediate Similarity	NPC119416
0.8333	Intermediate Similarity	NPC247312
0.8315	Intermediate Similarity	NPC472495
0.8315	Intermediate Similarity	NPC93778
0.8315	Intermediate Similarity	NPC472497
0.8315	Intermediate Similarity	NPC73064
0.8315	Intermediate Similarity	NPC475740
0.8315	Intermediate Similarity	NPC89747
0.8313	Intermediate Similarity	NPC5767
0.8313	Intermediate Similarity	NPC14112
0.8313	Intermediate Similarity	NPC86305
0.8313	Intermediate Similarity	NPC475742
0.8313	Intermediate Similarity	NPC278091
0.8313	Intermediate Similarity	NPC93662
0.8313	Intermediate Similarity	NPC78067
0.8295	Intermediate Similarity	NPC201655
0.8295	Intermediate Similarity	NPC470574
0.8295	Intermediate Similarity	NPC133954
0.8293	Intermediate Similarity	NPC199316
0.8293	Intermediate Similarity	NPC25511
0.8293	Intermediate Similarity	NPC192638
0.8293	Intermediate Similarity	NPC159497
0.8293	Intermediate Similarity	NPC62657
0.8293	Intermediate Similarity	NPC102313
0.828	Intermediate Similarity	NPC98639
0.828	Intermediate Similarity	NPC210214
0.828	Intermediate Similarity	NPC142352
0.8276	Intermediate Similarity	NPC472740
0.8261	Intermediate Similarity	NPC12722
0.8261	Intermediate Similarity	NPC287118
0.8261	Intermediate Similarity	NPC181594
0.8261	Intermediate Similarity	NPC144739
0.8261	Intermediate Similarity	NPC59170
0.8261	Intermediate Similarity	NPC473690
0.8261	Intermediate Similarity	NPC291373
0.8261	Intermediate Similarity	NPC471902
0.8256	Intermediate Similarity	NPC164210
0.8235	Intermediate Similarity	NPC192744
0.8222	Intermediate Similarity	NPC143767
0.8222	Intermediate Similarity	NPC328539
0.8222	Intermediate Similarity	NPC471722
0.8222	Intermediate Similarity	NPC474925
0.8222	Intermediate Similarity	NPC131470
0.8222	Intermediate Similarity	NPC146937
0.8222	Intermediate Similarity	NPC472802
0.8214	Intermediate Similarity	NPC149249
0.8214	Intermediate Similarity	NPC202540
0.8214	Intermediate Similarity	NPC212241
0.8214	Intermediate Similarity	NPC472746
0.8214	Intermediate Similarity	NPC248830
0.8214	Intermediate Similarity	NPC119355
0.8214	Intermediate Similarity	NPC221420
0.8211	Intermediate Similarity	NPC194196
0.8202	Intermediate Similarity	NPC474732
0.8202	Intermediate Similarity	NPC474778
0.8202	Intermediate Similarity	NPC474733
0.8202	Intermediate Similarity	NPC31564
0.8202	Intermediate Similarity	NPC213412
0.8202	Intermediate Similarity	NPC158393
0.8202	Intermediate Similarity	NPC145879
0.8191	Intermediate Similarity	NPC5532
0.8191	Intermediate Similarity	NPC61369
0.8191	Intermediate Similarity	NPC192428
0.8191	Intermediate Similarity	NPC29410
0.8191	Intermediate Similarity	NPC200054
0.8191	Intermediate Similarity	NPC469545
0.8182	Intermediate Similarity	NPC214043
0.8182	Intermediate Similarity	NPC221758
0.8182	Intermediate Similarity	NPC475509
0.8182	Intermediate Similarity	NPC85774
0.8182	Intermediate Similarity	NPC59453
0.8172	Intermediate Similarity	NPC104371
0.8172	Intermediate Similarity	NPC29247
0.8172	Intermediate Similarity	NPC111524
0.8172	Intermediate Similarity	NPC129004
0.8172	Intermediate Similarity	NPC101233
0.8172	Intermediate Similarity	NPC289539
0.8172	Intermediate Similarity	NPC191094
0.8172	Intermediate Similarity	NPC153775
0.8172	Intermediate Similarity	NPC47853
0.8172	Intermediate Similarity	NPC91772
0.8172	Intermediate Similarity	NPC302008
0.8172	Intermediate Similarity	NPC277399
0.8172	Intermediate Similarity	NPC209662
0.8172	Intermediate Similarity	NPC261333
0.8172	Intermediate Similarity	NPC292374
0.8172	Intermediate Similarity	NPC215271
0.8172	Intermediate Similarity	NPC64006
0.8171	Intermediate Similarity	NPC232112
0.8152	Intermediate Similarity	NPC211403
0.8152	Intermediate Similarity	NPC278106
0.8152	Intermediate Similarity	NPC250753
0.8152	Intermediate Similarity	NPC198242
0.8152	Intermediate Similarity	NPC471901
0.8132	Intermediate Similarity	NPC275740
0.8132	Intermediate Similarity	NPC309603
0.8132	Intermediate Similarity	NPC1015
0.8132	Intermediate Similarity	NPC31985
0.8132	Intermediate Similarity	NPC86319
0.8132	Intermediate Similarity	NPC473999
0.8118	Intermediate Similarity	NPC102708
0.8118	Intermediate Similarity	NPC42853

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 NPC472739 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	2234
0.2-0.3	4345
0.3-0.4	1670
0.4-0.5	317
0.5-0.6	132
0.6-0.7	182
0.7-0.8	75
0.8-0.85	6
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8941	High Similarity	NPD7520	Clinical (unspecified phase)
0.8488	Intermediate Similarity	NPD4788	Approved
0.8409	Intermediate Similarity	NPD3618	Phase 1
0.8352	Intermediate Similarity	NPD8034	Phase 2
0.8352	Intermediate Similarity	NPD8035	Phase 2
0.8352	Intermediate Similarity	NPD6079	Approved
0.8333	Intermediate Similarity	NPD5328	Approved
0.8191	Intermediate Similarity	NPD4697	Phase 3
0.8182	Intermediate Similarity	NPD4786	Approved
0.8049	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD7515	Phase 2
0.7955	Intermediate Similarity	NPD3667	Approved
0.7872	Intermediate Similarity	NPD4202	Approved
0.7812	Intermediate Similarity	NPD5222	Approved
0.7812	Intermediate Similarity	NPD5221	Approved
0.7812	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3665	Phase 1
0.7778	Intermediate Similarity	NPD3666	Approved
0.7778	Intermediate Similarity	NPD3133	Approved
0.7732	Intermediate Similarity	NPD5173	Approved
0.7674	Intermediate Similarity	NPD6117	Approved
0.7647	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD7748	Approved
0.7586	Intermediate Similarity	NPD6116	Phase 1
0.7576	Intermediate Similarity	NPD5286	Approved
0.7576	Intermediate Similarity	NPD5285	Approved
0.7576	Intermediate Similarity	NPD4696	Approved
0.7558	Intermediate Similarity	NPD3703	Phase 2
0.7551	Intermediate Similarity	NPD4755	Approved
0.7551	Intermediate Similarity	NPD7902	Approved
0.7528	Intermediate Similarity	NPD7525	Registered
0.75	Intermediate Similarity	NPD5223	Approved
0.75	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD4244	Approved
0.75	Intermediate Similarity	NPD6118	Approved
0.75	Intermediate Similarity	NPD6115	Approved
0.75	Intermediate Similarity	NPD4789	Approved
0.75	Intermediate Similarity	NPD4245	Approved
0.75	Intermediate Similarity	NPD6114	Approved
0.75	Intermediate Similarity	NPD6697	Approved
0.747	Intermediate Similarity	NPD5360	Phase 3
0.747	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD4633	Approved
0.7426	Intermediate Similarity	NPD5226	Approved
0.7426	Intermediate Similarity	NPD5225	Approved
0.7426	Intermediate Similarity	NPD5211	Phase 2
0.7426	Intermediate Similarity	NPD5224	Approved
0.7419	Intermediate Similarity	NPD5279	Phase 3
0.7419	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4700	Approved
0.7381	Intermediate Similarity	NPD3698	Phase 2
0.7368	Intermediate Similarity	NPD4753	Phase 2
0.7363	Intermediate Similarity	NPD4223	Phase 3
0.7363	Intermediate Similarity	NPD4221	Approved
0.7353	Intermediate Similarity	NPD5175	Approved
0.7353	Intermediate Similarity	NPD5174	Approved
0.7347	Intermediate Similarity	NPD5210	Approved
0.7347	Intermediate Similarity	NPD4629	Approved
0.7317	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5329	Approved
0.7282	Intermediate Similarity	NPD5141	Approved
0.7263	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7900	Approved
0.7245	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6881	Approved
0.7238	Intermediate Similarity	NPD6899	Approved
0.7222	Intermediate Similarity	NPD7645	Phase 2
0.7212	Intermediate Similarity	NPD6675	Approved
0.7212	Intermediate Similarity	NPD7128	Approved
0.7212	Intermediate Similarity	NPD6402	Approved
0.7212	Intermediate Similarity	NPD5739	Approved
0.7204	Intermediate Similarity	NPD3668	Phase 3
0.7204	Intermediate Similarity	NPD4197	Approved
0.7196	Intermediate Similarity	NPD6649	Approved
0.7196	Intermediate Similarity	NPD6650	Approved
0.7184	Intermediate Similarity	NPD4754	Approved
0.717	Intermediate Similarity	NPD6372	Approved
0.717	Intermediate Similarity	NPD6373	Approved
0.7159	Intermediate Similarity	NPD7339	Approved
0.7159	Intermediate Similarity	NPD6942	Approved
0.7143	Intermediate Similarity	NPD5697	Approved
0.7129	Intermediate Similarity	NPD7638	Approved
0.7111	Intermediate Similarity	NPD3671	Phase 1
0.7111	Intermediate Similarity	NPD3617	Approved
0.7103	Intermediate Similarity	NPD7290	Approved
0.7103	Intermediate Similarity	NPD6883	Approved
0.7103	Intermediate Similarity	NPD7102	Approved
0.7075	Intermediate Similarity	NPD5168	Approved
0.7075	Intermediate Similarity	NPD7320	Approved
0.7075	Intermediate Similarity	NPD6011	Approved
0.7075	Intermediate Similarity	NPD5128	Approved
0.7075	Intermediate Similarity	NPD4729	Approved
0.7075	Intermediate Similarity	NPD4730	Approved
0.7059	Intermediate Similarity	NPD7640	Approved
0.7059	Intermediate Similarity	NPD7639	Approved
0.7053	Intermediate Similarity	NPD4690	Approved
0.7053	Intermediate Similarity	NPD7521	Approved
0.7053	Intermediate Similarity	NPD7146	Approved
0.7053	Intermediate Similarity	NPD4689	Approved
0.7053	Intermediate Similarity	NPD5330	Approved
0.7053	Intermediate Similarity	NPD6409	Approved
0.7053	Intermediate Similarity	NPD4688	Approved
0.7053	Intermediate Similarity	NPD4693	Phase 3
0.7053	Intermediate Similarity	NPD5205	Approved
0.7053	Intermediate Similarity	NPD5690	Phase 2
0.7053	Intermediate Similarity	NPD4138	Approved
0.7053	Intermediate Similarity	NPD7334	Approved
0.7053	Intermediate Similarity	NPD6684	Approved
0.7048	Intermediate Similarity	NPD4767	Approved
0.7048	Intermediate Similarity	NPD4768	Approved
0.7037	Intermediate Similarity	NPD6869	Approved
0.7037	Intermediate Similarity	NPD6847	Approved
0.7037	Intermediate Similarity	NPD6617	Approved
0.7037	Intermediate Similarity	NPD8130	Phase 1
0.703	Intermediate Similarity	NPD6083	Phase 2
0.703	Intermediate Similarity	NPD6084	Phase 2
0.7027	Intermediate Similarity	NPD7115	Discovery
0.7011	Intermediate Similarity	NPD4758	Discontinued
0.7009	Intermediate Similarity	NPD6014	Approved
0.7009	Intermediate Similarity	NPD6012	Approved
0.7009	Intermediate Similarity	NPD6013	Approved
0.6981	Remote Similarity	NPD5701	Approved
0.6972	Remote Similarity	NPD6882	Approved
0.6972	Remote Similarity	NPD8297	Approved
0.6944	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5249	Phase 3
0.6944	Remote Similarity	NPD4634	Approved
0.6944	Remote Similarity	NPD5248	Approved
0.6944	Remote Similarity	NPD5169	Approved
0.6944	Remote Similarity	NPD5250	Approved
0.6944	Remote Similarity	NPD5247	Approved
0.6944	Remote Similarity	NPD5135	Approved
0.6944	Remote Similarity	NPD5251	Approved
0.6907	Remote Similarity	NPD5737	Approved
0.6907	Remote Similarity	NPD6903	Approved
0.6907	Remote Similarity	NPD6672	Approved
0.6889	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5127	Approved
0.6881	Remote Similarity	NPD5215	Approved
0.6881	Remote Similarity	NPD5217	Approved
0.6881	Remote Similarity	NPD5216	Approved
0.6881	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5280	Approved
0.6875	Remote Similarity	NPD4694	Approved
0.6848	Remote Similarity	NPD4195	Approved
0.6832	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4224	Phase 2
0.6818	Remote Similarity	NPD6081	Approved
0.6796	Remote Similarity	NPD5696	Approved
0.6786	Remote Similarity	NPD6868	Approved
0.6782	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4695	Discontinued
0.6757	Remote Similarity	NPD4632	Approved
0.6739	Remote Similarity	NPD5364	Discontinued
0.6705	Remote Similarity	NPD4747	Approved
0.6705	Remote Similarity	NPD4691	Approved
0.6702	Remote Similarity	NPD4692	Approved
0.6702	Remote Similarity	NPD4139	Approved
0.67	Remote Similarity	NPD5281	Approved
0.67	Remote Similarity	NPD5284	Approved
0.6696	Remote Similarity	NPD5167	Approved
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6637	Remote Similarity	NPD6274	Approved
0.6635	Remote Similarity	NPD5290	Discontinued
0.6633	Remote Similarity	NPD3573	Approved
0.6629	Remote Similarity	NPD5777	Approved
0.6609	Remote Similarity	NPD7101	Approved
0.6609	Remote Similarity	NPD7100	Approved
0.6604	Remote Similarity	NPD7632	Discontinued
0.6591	Remote Similarity	NPD4137	Phase 3
0.6579	Remote Similarity	NPD6317	Approved
0.6579	Remote Similarity	NPD6009	Approved
0.6574	Remote Similarity	NPD6008	Approved
0.6569	Remote Similarity	NPD6001	Approved
0.6555	Remote Similarity	NPD7507	Approved
0.6552	Remote Similarity	NPD6054	Approved
0.6531	Remote Similarity	NPD6098	Approved
0.6531	Remote Similarity	NPD4519	Discontinued
0.6531	Remote Similarity	NPD4623	Approved
0.6522	Remote Similarity	NPD6933	Approved
0.6522	Remote Similarity	NPD6314	Approved
0.6522	Remote Similarity	NPD6313	Approved
0.6517	Remote Similarity	NPD4787	Phase 1
0.65	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6080	Approved
0.65	Remote Similarity	NPD6673	Approved
0.65	Remote Similarity	NPD6904	Approved
0.6496	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5733	Approved
0.6484	Remote Similarity	NPD4058	Approved
0.646	Remote Similarity	NPD8133	Approved
0.6449	Remote Similarity	NPD5091	Approved
0.6446	Remote Similarity	NPD7736	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