NPASS Compound

Structure

NPC270586 OpenBabel07101718232D 38 43 0 0 1 0 0 0 0 0999 V2000 -7.9229 2.0806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5628 0.3864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1859 0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7375 2.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3486 4.3986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6284 1.0102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6065 0.8023 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 2.9781 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2538 1.3375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3194 1.9612 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3412 2.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2757 1.5454 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 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9885 2.7044 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6795 3.6554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9666 2.4965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 18 1 0 0 0 0 3 28 1 0 0 0 0 6 36 1 0 0 0 0 7 37 1 0 0 0 0 8 9 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 29 1 0 0 0 0 14 15 1 0 0 0 0 14 28 1 0 0 0 0 15 31 1 0 0 0 0 16 24 1 0 0 0 0 16 25 1 0 0 0 0 17 31 1 0 0 0 0 19 8 1 1 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 20 28 1 1 0 0 0 21 18 1 1 0 0 0 21 38 1 0 0 0 0 22 29 1 6 0 0 0 22 31 1 0 0 0 0 23 30 1 1 0 0 0 23 32 1 0 0 0 0 24 30 1 1 0 0 0 24 33 1 0 0 0 0 25 32 1 6 0 0 0 25 34 1 0 0 0 0 26 36 1 6 0 0 0 26 38 1 0 0 0 0 27 30 1 0 0 0 0 27 35 2 0 0 0 0 27 37 1 0 0 0 0 28 29 1 1 0 0 0 29 4 1 6 0 0 0 30 5 1 1 0 0 0 31 32 1 6 0 0 0 32 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.36
Volume:	558.158
LogP:	4.64
LogD:	3.835
LogS:	-4.314
# Rotatable Bonds:	5
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.381
Synthetic Accessibility Score:	6.149
Fsp3:	0.906
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.19
MDCK Permeability:	1.2347240044618957e-05
Pgp-inhibitor:	0.897
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.54

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.266
Plasma Protein Binding (PPB):	83.39327239990234%
Volume Distribution (VD):	1.726
Pgp-substrate:	10.836654663085938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.925
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.215
CYP3A4-inhibitor:	0.961
CYP3A4-substrate:	0.71

ADMET: Excretion

Clearance (CL):	8.318
Half-life (T1/2):	0.085

ADMET: Toxicity

hERG Blockers:	0.294
Human Hepatotoxicity (H-HT):	0.581
Drug-inuced Liver Injury (DILI):	0.055
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.88
Maximum Recommended Daily Dose:	0.891
Skin Sensitization:	0.826
Carcinogencity:	0.843
Eye Corrosion:	0.01
Eye Irritation:	0.011
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC270586

Natural Product ID:	NPC270586
*Common Name:**	QPYCAQVRIHEGFV-TXMWYVDOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QPYCAQVRIHEGFV-TXMWYVDOSA-N
Standard InCHI:	InChI=1S/C32H50O6/c1-18(2)21-9-8-19(26(36-6)38-21)20-12-13-29(4)22-10-11-23-30(5,27(35)37-7)24(33)16-25(34)32(23)17-31(22,32)15-14-28(20,29)3/h19-26,33-34H,1,8-17H2,2-7H3/t19-,20-,21+,22+,23+,24+,25+,26+,28-,29+,30+,31+,32-/m1/s1
SMILES:	C=C(C)[C@@H]1CC[C@H]([C@H]2CC[C@@]3(C)[C@@H]4CC[C@H]5[C@@](C)([C@H](C[C@@H]([C@]65C[C@@]46CC[C@]23C)O)O)C(=O)OC)[C@@H](OC)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL118708
PubChem CID:	44344630
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650080]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10785422]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11277757]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	leaves	Khon Kaen, Thailand	2006-AUG	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9934464]

☑ 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
ED50	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.	ED50	=	18.11	uM	PMID[473791]

☑ 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 NPC270586 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	285
0.1-0.2	2081
0.2-0.3	5980
0.3-0.4	11560
0.4-0.5	9889
0.5-0.6	5769
0.6-0.7	4422
0.7-0.8	2556
0.8-0.85	138
0.85-0.9	16
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.902	High Similarity	NPC94906
0.8932	High Similarity	NPC75941
0.8922	High Similarity	NPC472028
0.8889	High Similarity	NPC470311
0.8879	High Similarity	NPC471250
0.8846	High Similarity	NPC124544
0.8835	High Similarity	NPC37047
0.8835	High Similarity	NPC180733
0.8835	High Similarity	NPC41971
0.8727	High Similarity	NPC73986
0.8716	High Similarity	NPC471251
0.8627	High Similarity	NPC263135
0.8627	High Similarity	NPC288906
0.8624	High Similarity	NPC124053
0.8545	High Similarity	NPC329953
0.8545	High Similarity	NPC272242
0.8545	High Similarity	NPC11035
0.8468	Intermediate Similarity	NPC243572
0.8468	Intermediate Similarity	NPC476964
0.8468	Intermediate Similarity	NPC470543
0.8462	Intermediate Similarity	NPC469810
0.844	Intermediate Similarity	NPC88744
0.8426	Intermediate Similarity	NPC295366
0.8426	Intermediate Similarity	NPC285927
0.8426	Intermediate Similarity	NPC4115
0.8426	Intermediate Similarity	NPC12823
0.8421	Intermediate Similarity	NPC239293
0.8411	Intermediate Similarity	NPC139347
0.8407	Intermediate Similarity	NPC469820
0.8407	Intermediate Similarity	NPC469823
0.8393	Intermediate Similarity	NPC102619
0.8393	Intermediate Similarity	NPC146563
0.8365	Intermediate Similarity	NPC234564
0.8364	Intermediate Similarity	NPC469983
0.8364	Intermediate Similarity	NPC473844
0.8364	Intermediate Similarity	NPC476759
0.8364	Intermediate Similarity	NPC91583
0.8364	Intermediate Similarity	NPC240125
0.8364	Intermediate Similarity	NPC51947
0.8349	Intermediate Similarity	NPC61071
0.8349	Intermediate Similarity	NPC263729
0.8319	Intermediate Similarity	NPC471357
0.8319	Intermediate Similarity	NPC117702
0.8319	Intermediate Similarity	NPC54395
0.8319	Intermediate Similarity	NPC146456
0.8319	Intermediate Similarity	NPC469757
0.8318	Intermediate Similarity	NPC170615
0.8318	Intermediate Similarity	NPC94919
0.8288	Intermediate Similarity	NPC98633
0.8288	Intermediate Similarity	NPC130302
0.8288	Intermediate Similarity	NPC255655
0.8273	Intermediate Similarity	NPC232133
0.8273	Intermediate Similarity	NPC230888
0.8273	Intermediate Similarity	NPC469733
0.8273	Intermediate Similarity	NPC469729
0.8273	Intermediate Similarity	NPC224414
0.8261	Intermediate Similarity	NPC469822
0.8257	Intermediate Similarity	NPC165405
0.8252	Intermediate Similarity	NPC473690
0.8252	Intermediate Similarity	NPC471902
0.8252	Intermediate Similarity	NPC287118
0.8246	Intermediate Similarity	NPC137414
0.823	Intermediate Similarity	NPC285086
0.8224	Intermediate Similarity	NPC71706
0.8224	Intermediate Similarity	NPC46848
0.8214	Intermediate Similarity	NPC204392
0.8214	Intermediate Similarity	NPC91838
0.8214	Intermediate Similarity	NPC240734
0.8214	Intermediate Similarity	NPC1876
0.8214	Intermediate Similarity	NPC275668
0.8208	Intermediate Similarity	NPC474793
0.8205	Intermediate Similarity	NPC470478
0.8198	Intermediate Similarity	NPC469744
0.819	Intermediate Similarity	NPC329910
0.819	Intermediate Similarity	NPC317573
0.8182	Intermediate Similarity	NPC469754
0.8182	Intermediate Similarity	NPC469751
0.8182	Intermediate Similarity	NPC284406
0.8182	Intermediate Similarity	NPC469755
0.8182	Intermediate Similarity	NPC469753
0.8182	Intermediate Similarity	NPC180079
0.8182	Intermediate Similarity	NPC89514
0.8182	Intermediate Similarity	NPC469752
0.8182	Intermediate Similarity	NPC471358
0.8182	Intermediate Similarity	NPC10823
0.8182	Intermediate Similarity	NPC470952
0.8182	Intermediate Similarity	NPC471360
0.8182	Intermediate Similarity	NPC88833
0.8182	Intermediate Similarity	NPC70542
0.8182	Intermediate Similarity	NPC86159
0.8182	Intermediate Similarity	NPC471359
0.8182	Intermediate Similarity	NPC219085
0.8182	Intermediate Similarity	NPC9499
0.8182	Intermediate Similarity	NPC251866
0.8182	Intermediate Similarity	NPC471352
0.8182	Intermediate Similarity	NPC17896
0.8182	Intermediate Similarity	NPC6108
0.8182	Intermediate Similarity	NPC471361
0.8182	Intermediate Similarity	NPC197707
0.8182	Intermediate Similarity	NPC96333
0.8174	Intermediate Similarity	NPC473304
0.8174	Intermediate Similarity	NPC156651
0.8165	Intermediate Similarity	NPC101842
0.8165	Intermediate Similarity	NPC202793
0.8158	Intermediate Similarity	NPC469821
0.8155	Intermediate Similarity	NPC475416
0.8155	Intermediate Similarity	NPC471901
0.8148	Intermediate Similarity	NPC309388
0.8148	Intermediate Similarity	NPC475803
0.8148	Intermediate Similarity	NPC286519
0.8148	Intermediate Similarity	NPC214946
0.8148	Intermediate Similarity	NPC193934
0.8148	Intermediate Similarity	NPC275990
0.8148	Intermediate Similarity	NPC271980
0.8148	Intermediate Similarity	NPC88203
0.8148	Intermediate Similarity	NPC76866
0.8148	Intermediate Similarity	NPC304832
0.8148	Intermediate Similarity	NPC148628
0.8148	Intermediate Similarity	NPC246736
0.8142	Intermediate Similarity	NPC471245
0.813	Intermediate Similarity	NPC32793
0.813	Intermediate Similarity	NPC247190
0.813	Intermediate Similarity	NPC116075
0.813	Intermediate Similarity	NPC146857
0.813	Intermediate Similarity	NPC469749
0.8125	Intermediate Similarity	NPC49730
0.8125	Intermediate Similarity	NPC98069
0.8125	Intermediate Similarity	NPC106760
0.8125	Intermediate Similarity	NPC476766
0.812	Intermediate Similarity	NPC470312
0.8113	Intermediate Similarity	NPC253586
0.8108	Intermediate Similarity	NPC476765
0.8108	Intermediate Similarity	NPC63841
0.8108	Intermediate Similarity	NPC163216
0.8095	Intermediate Similarity	NPC266431
0.8095	Intermediate Similarity	NPC470229
0.8095	Intermediate Similarity	NPC470232
0.8091	Intermediate Similarity	NPC28791
0.8091	Intermediate Similarity	NPC103172
0.8091	Intermediate Similarity	NPC37600
0.8091	Intermediate Similarity	NPC164600
0.8087	Intermediate Similarity	NPC88945
0.8077	Intermediate Similarity	NPC475061
0.8073	Intermediate Similarity	NPC470310
0.8073	Intermediate Similarity	NPC312900
0.8067	Intermediate Similarity	NPC27363
0.8065	Intermediate Similarity	NPC329636
0.8056	Intermediate Similarity	NPC471790
0.8056	Intermediate Similarity	NPC163963
0.8056	Intermediate Similarity	NPC14634
0.8056	Intermediate Similarity	NPC236585
0.8056	Intermediate Similarity	NPC289148
0.8056	Intermediate Similarity	NPC253886
0.8056	Intermediate Similarity	NPC52899
0.8056	Intermediate Similarity	NPC121218
0.8053	Intermediate Similarity	NPC250481
0.8053	Intermediate Similarity	NPC122339
0.8053	Intermediate Similarity	NPC94650
0.8053	Intermediate Similarity	NPC285410
0.8053	Intermediate Similarity	NPC263827
0.8039	Intermediate Similarity	NPC146937
0.8037	Intermediate Similarity	NPC20479
0.8037	Intermediate Similarity	NPC38296
0.8037	Intermediate Similarity	NPC28864
0.8037	Intermediate Similarity	NPC119036
0.8037	Intermediate Similarity	NPC162459
0.8037	Intermediate Similarity	NPC471038
0.8037	Intermediate Similarity	NPC38471
0.8037	Intermediate Similarity	NPC98837
0.8036	Intermediate Similarity	NPC8431
0.8036	Intermediate Similarity	NPC257082
0.8036	Intermediate Similarity	NPC285298
0.8019	Intermediate Similarity	NPC327788
0.8018	Intermediate Similarity	NPC86852
0.8018	Intermediate Similarity	NPC469746
0.8018	Intermediate Similarity	NPC186054
0.8018	Intermediate Similarity	NPC251824
0.8018	Intermediate Similarity	NPC287269
0.8017	Intermediate Similarity	NPC329784
0.8017	Intermediate Similarity	NPC240070
0.8017	Intermediate Similarity	NPC42399
0.8017	Intermediate Similarity	NPC179412
0.8017	Intermediate Similarity	NPC298841
0.8017	Intermediate Similarity	NPC471356
0.8	Intermediate Similarity	NPC194716
0.8	Intermediate Similarity	NPC476763
0.8	Intermediate Similarity	NPC476764
0.8	Intermediate Similarity	NPC116024
0.8	Intermediate Similarity	NPC470385
0.8	Intermediate Similarity	NPC470386
0.8	Intermediate Similarity	NPC47853
0.8	Intermediate Similarity	NPC469982
0.8	Intermediate Similarity	NPC475118
0.8	Intermediate Similarity	NPC201763
0.8	Intermediate Similarity	NPC472274
0.8	Intermediate Similarity	NPC318135
0.7982	Intermediate Similarity	NPC473303
0.7982	Intermediate Similarity	NPC40608
0.7982	Intermediate Similarity	NPC471244
0.7967	Intermediate Similarity	NPC173347

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 NPC270586 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	2372
0.2-0.3	3967
0.3-0.4	1661
0.4-0.5	430
0.5-0.6	276
0.6-0.7	137
0.7-0.8	27
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.823	Intermediate Similarity	NPD8133	Approved
0.8182	Intermediate Similarity	NPD7319	Approved
0.7934	Intermediate Similarity	NPD7507	Approved
0.7661	Intermediate Similarity	NPD7736	Approved
0.7642	Intermediate Similarity	NPD8034	Phase 2
0.7642	Intermediate Similarity	NPD8035	Phase 2
0.7573	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD7328	Approved
0.75	Intermediate Similarity	NPD7327	Approved
0.748	Intermediate Similarity	NPD8328	Phase 3
0.7478	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD7639	Approved
0.7477	Intermediate Similarity	NPD7640	Approved
0.7459	Intermediate Similarity	NPD8378	Approved
0.7459	Intermediate Similarity	NPD8335	Approved
0.7459	Intermediate Similarity	NPD8296	Approved
0.7459	Intermediate Similarity	NPD8380	Approved
0.7459	Intermediate Similarity	NPD8379	Approved
0.744	Intermediate Similarity	NPD8293	Discontinued
0.7438	Intermediate Similarity	NPD7516	Approved
0.7377	Intermediate Similarity	NPD8294	Approved
0.7377	Intermediate Similarity	NPD8377	Approved
0.7328	Intermediate Similarity	NPD6686	Approved
0.7317	Intermediate Similarity	NPD8033	Approved
0.7265	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6370	Approved
0.7241	Intermediate Similarity	NPD6412	Phase 2
0.7217	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7492	Approved
0.7131	Intermediate Similarity	NPD7115	Discovery
0.7097	Intermediate Similarity	NPD6054	Approved
0.7097	Intermediate Similarity	NPD6059	Approved
0.7087	Intermediate Similarity	NPD6616	Approved
0.7083	Intermediate Similarity	NPD6882	Approved
0.7059	Intermediate Similarity	NPD6697	Approved
0.7059	Intermediate Similarity	NPD6114	Approved
0.7059	Intermediate Similarity	NPD6118	Approved
0.7059	Intermediate Similarity	NPD6115	Approved
0.7043	Intermediate Similarity	NPD7632	Discontinued
0.704	Intermediate Similarity	NPD8515	Approved
0.704	Intermediate Similarity	NPD8517	Approved
0.704	Intermediate Similarity	NPD8513	Phase 3
0.704	Intermediate Similarity	NPD8516	Approved
0.7031	Intermediate Similarity	NPD7078	Approved
0.7009	Intermediate Similarity	NPD5739	Approved
0.7009	Intermediate Similarity	NPD6402	Approved
0.7009	Intermediate Similarity	NPD6675	Approved
0.7009	Intermediate Similarity	NPD7128	Approved
0.6905	Remote Similarity	NPD7503	Approved
0.6905	Remote Similarity	NPD6015	Approved
0.6905	Remote Similarity	NPD6016	Approved
0.6891	Remote Similarity	NPD6881	Approved
0.6891	Remote Similarity	NPD7320	Approved
0.6891	Remote Similarity	NPD6899	Approved
0.6875	Remote Similarity	NPD7748	Approved
0.6863	Remote Similarity	NPD6117	Approved
0.686	Remote Similarity	NPD8130	Phase 1
0.6855	Remote Similarity	NPD6009	Approved
0.685	Remote Similarity	NPD5988	Approved
0.6833	Remote Similarity	NPD6373	Approved
0.6833	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6372	Approved
0.6825	Remote Similarity	NPD6319	Approved
0.6818	Remote Similarity	NPD5328	Approved
0.6807	Remote Similarity	NPD5697	Approved
0.6807	Remote Similarity	NPD5701	Approved
0.6803	Remote Similarity	NPD8297	Approved
0.6796	Remote Similarity	NPD6116	Phase 1
0.6786	Remote Similarity	NPD6399	Phase 3
0.6777	Remote Similarity	NPD7290	Approved
0.6777	Remote Similarity	NPD6883	Approved
0.6777	Remote Similarity	NPD7102	Approved
0.6772	Remote Similarity	NPD6921	Approved
0.6723	Remote Similarity	NPD6008	Approved
0.6721	Remote Similarity	NPD6847	Approved
0.6721	Remote Similarity	NPD6617	Approved
0.6721	Remote Similarity	NPD6869	Approved
0.6721	Remote Similarity	NPD6649	Approved
0.6721	Remote Similarity	NPD6650	Approved
0.6696	Remote Similarity	NPD6411	Approved
0.6696	Remote Similarity	NPD7637	Suspended
0.6696	Remote Similarity	NPD7902	Approved
0.6696	Remote Similarity	NPD7515	Phase 2
0.6696	Remote Similarity	NPD6079	Approved
0.6694	Remote Similarity	NPD6014	Approved
0.6694	Remote Similarity	NPD6013	Approved
0.6694	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD4632	Approved
0.6612	Remote Similarity	NPD6011	Approved
0.6602	Remote Similarity	NPD3703	Phase 2
0.6591	Remote Similarity	NPD6033	Approved
0.6585	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6084	Phase 2
0.6552	Remote Similarity	NPD4755	Approved
0.6552	Remote Similarity	NPD6083	Phase 2
0.6532	Remote Similarity	NPD6053	Discontinued
0.6518	Remote Similarity	NPD6101	Approved
0.6518	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4786	Approved
0.6508	Remote Similarity	NPD6940	Discontinued
0.6504	Remote Similarity	NPD4634	Approved
0.6496	Remote Similarity	NPD4225	Approved
0.6491	Remote Similarity	NPD8171	Discontinued
0.6491	Remote Similarity	NPD5778	Approved
0.6491	Remote Similarity	NPD5779	Approved
0.6471	Remote Similarity	NPD5211	Phase 2
0.6466	Remote Similarity	NPD5221	Approved
0.6466	Remote Similarity	NPD5222	Approved
0.6466	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD4697	Phase 3
0.6449	Remote Similarity	NPD6928	Phase 2
0.6441	Remote Similarity	NPD4700	Approved
0.6441	Remote Similarity	NPD4696	Approved
0.6441	Remote Similarity	NPD5286	Approved
0.6441	Remote Similarity	NPD5285	Approved
0.6435	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD7900	Approved
0.6429	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4788	Approved
0.6412	Remote Similarity	NPD6067	Discontinued
0.641	Remote Similarity	NPD5173	Approved
0.6396	Remote Similarity	NPD3618	Phase 1
0.6393	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD8074	Phase 3
0.6385	Remote Similarity	NPD5983	Phase 2
0.6379	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6868	Approved
0.6378	Remote Similarity	NPD6274	Approved
0.6364	Remote Similarity	NPD5141	Approved
0.6357	Remote Similarity	NPD7101	Approved
0.6357	Remote Similarity	NPD7100	Approved
0.6333	Remote Similarity	NPD5224	Approved
0.6333	Remote Similarity	NPD5226	Approved
0.6333	Remote Similarity	NPD4633	Approved
0.6333	Remote Similarity	NPD5225	Approved
0.633	Remote Similarity	NPD3667	Approved
0.6316	Remote Similarity	NPD6336	Discontinued
0.6311	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7525	Registered
0.6286	Remote Similarity	NPD3702	Approved
0.6283	Remote Similarity	NPD6672	Approved
0.6283	Remote Similarity	NPD5737	Approved
0.6281	Remote Similarity	NPD5174	Approved
0.6281	Remote Similarity	NPD5175	Approved
0.6279	Remote Similarity	NPD6335	Approved
0.626	Remote Similarity	NPD6908	Approved
0.626	Remote Similarity	NPD6909	Approved
0.625	Remote Similarity	NPD1700	Approved
0.625	Remote Similarity	NPD6684	Approved
0.625	Remote Similarity	NPD6409	Approved
0.625	Remote Similarity	NPD5330	Approved
0.625	Remote Similarity	NPD7521	Approved
0.625	Remote Similarity	NPD7334	Approved
0.625	Remote Similarity	NPD7146	Approved
0.625	Remote Similarity	NPD5223	Approved
0.6239	Remote Similarity	NPD5695	Phase 3
0.6218	Remote Similarity	NPD5696	Approved
0.6207	Remote Similarity	NPD4202	Approved
0.6202	Remote Similarity	NPD6317	Approved
0.6195	Remote Similarity	NPD3573	Approved
0.619	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7839	Suspended
0.6179	Remote Similarity	NPD4768	Approved
0.6179	Remote Similarity	NPD4767	Approved
0.6154	Remote Similarity	NPD6314	Approved
0.6154	Remote Similarity	NPD6313	Approved
0.6148	Remote Similarity	NPD4754	Approved
0.614	Remote Similarity	NPD6903	Approved
0.6126	Remote Similarity	NPD6695	Phase 3
0.6121	Remote Similarity	NPD5693	Phase 1
0.6117	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6371	Approved
0.6087	Remote Similarity	NPD6051	Approved
0.6087	Remote Similarity	NPD7799	Discontinued
0.6087	Remote Similarity	NPD4753	Phase 2
0.608	Remote Similarity	NPD4729	Approved
0.608	Remote Similarity	NPD5128	Approved
0.608	Remote Similarity	NPD4730	Approved
0.6071	Remote Similarity	NPD3133	Approved
0.6071	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD3665	Phase 1
0.6071	Remote Similarity	NPD3666	Approved
0.6055	Remote Similarity	NPD7645	Phase 2
0.6053	Remote Similarity	NPD7750	Discontinued
0.6043	Remote Similarity	NPD8338	Approved
0.6036	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD46	Approved
0.6034	Remote Similarity	NPD6698	Approved
0.6033	Remote Similarity	NPD8418	Phase 2
0.6017	Remote Similarity	NPD6001	Approved
0.6015	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD6914	Discontinued
0.6	Remote Similarity	NPD5777	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