NPASS Compound

Structure

NPC471072 OpenBabel07101718182D 43 44 0 0 1 0 0 0 0 0999 V2000 -19.9186 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1603 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -20.7846 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -20.7846 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.9186 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.9186 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.0526 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.0526 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.1865 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.3205 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.4545 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.5885 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 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 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 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 -6.0622 0.5000 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 0.5000 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 -8.6603 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.5263 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 -8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 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 -7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 30 1 0 0 0 0 3 37 1 0 0 0 0 4 37 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 2 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 35 1 0 0 0 0 21 25 1 0 0 0 0 21 30 1 0 0 0 0 22 24 2 0 0 0 0 22 31 1 0 0 0 0 23 26 2 0 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 26 36 1 0 0 0 0 27 28 1 0 0 0 0 27 30 2 0 0 0 0 28 41 1 0 0 0 0 29 32 2 0 0 0 0 29 33 1 0 0 0 0 31 33 2 0 0 0 0 32 41 1 0 0 0 0 33 42 1 0 0 0 0 34 25 1 6 0 0 0 34 37 1 0 0 0 0 34 43 1 0 0 0 0 35 38 2 0 0 0 0 35 43 1 0 0 0 0 36 39 2 0 0 0 0 36 42 1 0 0 0 0 37 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	596.41
Volume:	663.045
LogP:	8.632
LogD:	5.297
LogS:	-3.351
# Rotatable Bonds:	24
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.059
Synthetic Accessibility Score:	3.538
Fsp3:	0.622
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.929
MDCK Permeability:	3.124369686702266e-05
Pgp-inhibitor:	0.447
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.14
Plasma Protein Binding (PPB):	101.58826446533203%
Volume Distribution (VD):	2.71
Pgp-substrate:	0.7800916433334351%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.189
CYP2C19-inhibitor:	0.278
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.092
CYP2C9-substrate:	0.987
CYP2D6-inhibitor:	0.344
CYP2D6-substrate:	0.571
CYP3A4-inhibitor:	0.459
CYP3A4-substrate:	0.114

ADMET: Excretion

Clearance (CL):	4.511
Half-life (T1/2):	0.392

ADMET: Toxicity

hERG Blockers:	0.472
Human Hepatotoxicity (H-HT):	0.642
Drug-inuced Liver Injury (DILI):	0.568
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.567
Skin Sensitization:	0.969
Carcinogencity:	0.049
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.274

Download Data

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

Natural Product: NPC471072

Natural Product ID:	NPC471072
*Common Name:**	R-(+)-Marmin-6'-Cis-Vaccenoate
IUPAC Name:	[(E,3R)-2-hydroxy-2,6-dimethyl-8-(2-oxochromen-7-yl)oxyoct-6-en-3-yl] (Z)-octadec-11-enoate
Synonyms:	R-(+)-Marmin-6'-cis-vaccenoate
Standard InCHIKey:	RGIBFXLLLNMYOY-YZLPGLLOSA-N
Standard InCHI:	InChI=1S/C37H56O6/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-35(38)43-34(37(3,4)40)25-21-30(2)27-28-41-32-24-22-31-23-26-36(39)42-33(31)29-32/h10-11,22-24,26-27,29,34,40H,5-9,12-21,25,28H2,1-4H3/b11-10-,30-27+/t34-/m1/s1
SMILES:	CCCCCC/C=CCCCCCCCCCC(=O)O[C@@H](C(O)(C)C)CC/C(=C/COc1ccc2c(c1)oc(=O)cc2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2346918
PubChem CID:	71584691
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins 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
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18760601]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	bark	n.a.	PMID[21875114]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23434131]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26247834]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30579794]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Others	5

Activity Type	# Activity
Others	3
PROTEIN COMPLEX	200

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	-6.0	%	PMID[478450]
NPT2	Others	Unspecified		Inhibition	=	5.0	%	PMID[478450]
NPT2	Others	Unspecified		Inhibition	=	20.0	%	PMID[478450]
NPT22409	PROTEIN COMPLEX	Mitochondrial complex I (NADH dehydrogenase)	Homo sapiens	Inhibition	=	20.0	%	PMID[478450]
NPT22409	PROTEIN COMPLEX	Mitochondrial complex I (NADH dehydrogenase)	Homo sapiens	IC50	>	30000.0	nM	PMID[478450]

☑ 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 NPC471072 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	344
0.1-0.2	1415
0.2-0.3	3673
0.3-0.4	8452
0.4-0.5	10217
0.5-0.6	4118
0.6-0.7	6143
0.7-0.8	5203
0.8-0.85	2349
0.85-0.9	611
0.9-0.95	156
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471070
1.0	High Similarity	NPC471071
0.9924	High Similarity	NPC471068
0.9924	High Similarity	NPC471069
0.9323	High Similarity	NPC469449
0.9318	High Similarity	NPC267336
0.9318	High Similarity	NPC272650
0.9318	High Similarity	NPC29734
0.9242	High Similarity	NPC113098
0.9191	High Similarity	NPC155963
0.9124	High Similarity	NPC151946
0.9058	High Similarity	NPC312881
0.9044	High Similarity	NPC472525
0.8993	High Similarity	NPC195357
0.8993	High Similarity	NPC287286
0.8993	High Similarity	NPC152771
0.8978	High Similarity	NPC26954
0.8978	High Similarity	NPC38099
0.8971	High Similarity	NPC213173
0.8971	High Similarity	NPC98179
0.8971	High Similarity	NPC253574
0.8971	High Similarity	NPC224475
0.8971	High Similarity	NPC180716
0.8971	High Similarity	NPC62366
0.8947	High Similarity	NPC469453
0.8936	High Similarity	NPC471824
0.8913	High Similarity	NPC232246
0.8913	High Similarity	NPC153818
0.8905	High Similarity	NPC61499
0.8905	High Similarity	NPC33986
0.8897	High Similarity	NPC222036
0.8897	High Similarity	NPC7526
0.8872	High Similarity	NPC224774
0.8872	High Similarity	NPC258567
0.8872	High Similarity	NPC121740
0.8857	High Similarity	NPC155552
0.8849	High Similarity	NPC279573
0.8849	High Similarity	NPC211110
0.8841	High Similarity	NPC78746
0.8841	High Similarity	NPC188380
0.8841	High Similarity	NPC283331
0.8841	High Similarity	NPC128529
0.8841	High Similarity	NPC471630
0.8841	High Similarity	NPC55615
0.8841	High Similarity	NPC160727
0.8841	High Similarity	NPC283019
0.8841	High Similarity	NPC224543
0.8841	High Similarity	NPC149320
0.8841	High Similarity	NPC177281
0.8841	High Similarity	NPC476455
0.8832	High Similarity	NPC74655
0.8832	High Similarity	NPC287182
0.8832	High Similarity	NPC260265
0.8832	High Similarity	NPC195343
0.8832	High Similarity	NPC50896
0.8832	High Similarity	NPC164269
0.8832	High Similarity	NPC55149
0.8832	High Similarity	NPC166672
0.8832	High Similarity	NPC100986
0.8832	High Similarity	NPC84894
0.8832	High Similarity	NPC47163
0.8832	High Similarity	NPC319859
0.8832	High Similarity	NPC307412
0.8832	High Similarity	NPC204353
0.8832	High Similarity	NPC326600
0.8832	High Similarity	NPC127888
0.8832	High Similarity	NPC18804
0.8832	High Similarity	NPC198381
0.8832	High Similarity	NPC267412
0.8828	High Similarity	NPC103116
0.8824	High Similarity	NPC14248
0.8806	High Similarity	NPC185066
0.8786	High Similarity	NPC71903
0.8777	High Similarity	NPC184861
0.8777	High Similarity	NPC294456
0.8777	High Similarity	NPC212124
0.8777	High Similarity	NPC281014
0.8777	High Similarity	NPC225106
0.8768	High Similarity	NPC86892
0.8768	High Similarity	NPC472424
0.8768	High Similarity	NPC471625
0.8768	High Similarity	NPC471909
0.8768	High Similarity	NPC281241
0.8759	High Similarity	NPC31849
0.8759	High Similarity	NPC167111
0.8759	High Similarity	NPC207002
0.8759	High Similarity	NPC318400
0.8759	High Similarity	NPC471910
0.8759	High Similarity	NPC133956
0.8759	High Similarity	NPC296624
0.8741	High Similarity	NPC474289
0.8732	High Similarity	NPC229916
0.8723	High Similarity	NPC170812
0.8723	High Similarity	NPC310370
0.8723	High Similarity	NPC183642
0.8714	High Similarity	NPC327612
0.8714	High Similarity	NPC307883
0.8714	High Similarity	NPC73078
0.8714	High Similarity	NPC148738
0.8714	High Similarity	NPC319870
0.8686	High Similarity	NPC175159
0.8667	High Similarity	NPC472519
0.8647	High Similarity	NPC201667
0.8647	High Similarity	NPC73413
0.8633	High Similarity	NPC229128
0.8633	High Similarity	NPC469675
0.8626	High Similarity	NPC180006
0.8626	High Similarity	NPC163200
0.8626	High Similarity	NPC235190
0.8623	High Similarity	NPC54503
0.8623	High Similarity	NPC2363
0.8623	High Similarity	NPC55147
0.8613	High Similarity	NPC472517
0.8611	High Similarity	NPC469701
0.8611	High Similarity	NPC295696
0.8611	High Similarity	NPC85624
0.8603	High Similarity	NPC168710
0.8593	High Similarity	NPC243688
0.8592	High Similarity	NPC300611
0.8582	High Similarity	NPC221046
0.8571	High Similarity	NPC109675
0.8571	High Similarity	NPC223616
0.8571	High Similarity	NPC273772
0.8571	High Similarity	NPC472518
0.8571	High Similarity	NPC317045
0.8571	High Similarity	NPC246177
0.8571	High Similarity	NPC107197
0.8552	High Similarity	NPC205361
0.8551	High Similarity	NPC194277
0.854	High Similarity	NPC80170
0.8531	High Similarity	NPC184053
0.8523	High Similarity	NPC256141
0.8514	High Similarity	NPC180351
0.8511	High Similarity	NPC131198
0.8507	High Similarity	NPC27671
0.8503	High Similarity	NPC146388
0.8496	Intermediate Similarity	NPC96286
0.8496	Intermediate Similarity	NPC248429
0.8493	Intermediate Similarity	NPC296377
0.8493	Intermediate Similarity	NPC471764
0.8493	Intermediate Similarity	NPC87950
0.8489	Intermediate Similarity	NPC163557
0.8483	Intermediate Similarity	NPC71739
0.8483	Intermediate Similarity	NPC76657
0.8473	Intermediate Similarity	NPC281356
0.8473	Intermediate Similarity	NPC298796
0.8472	Intermediate Similarity	NPC183646
0.8472	Intermediate Similarity	NPC119640
0.8462	Intermediate Similarity	NPC215512
0.8462	Intermediate Similarity	NPC476442
0.8451	Intermediate Similarity	NPC253616
0.8451	Intermediate Similarity	NPC332594
0.8446	Intermediate Similarity	NPC146014
0.8446	Intermediate Similarity	NPC100818
0.8444	Intermediate Similarity	NPC244495
0.8444	Intermediate Similarity	NPC93219
0.8444	Intermediate Similarity	NPC471827
0.8444	Intermediate Similarity	NPC471828
0.844	Intermediate Similarity	NPC103409
0.8435	Intermediate Similarity	NPC139839
0.8435	Intermediate Similarity	NPC169510
0.8435	Intermediate Similarity	NPC14875
0.8433	Intermediate Similarity	NPC315807
0.8425	Intermediate Similarity	NPC287275
0.8425	Intermediate Similarity	NPC171656
0.8425	Intermediate Similarity	NPC212697
0.8421	Intermediate Similarity	NPC52247
0.8421	Intermediate Similarity	NPC187868
0.8417	Intermediate Similarity	NPC307289
0.8414	Intermediate Similarity	NPC471763
0.8414	Intermediate Similarity	NPC476457
0.8411	Intermediate Similarity	NPC108937
0.8411	Intermediate Similarity	NPC279218
0.8409	Intermediate Similarity	NPC474874
0.8409	Intermediate Similarity	NPC31314
0.8406	Intermediate Similarity	NPC32463
0.8406	Intermediate Similarity	NPC19242
0.8403	Intermediate Similarity	NPC471587
0.8397	Intermediate Similarity	NPC471823
0.8397	Intermediate Similarity	NPC96705
0.8397	Intermediate Similarity	NPC265547
0.8397	Intermediate Similarity	NPC152306
0.8394	Intermediate Similarity	NPC199204
0.8394	Intermediate Similarity	NPC157212
0.8382	Intermediate Similarity	NPC234109
0.8382	Intermediate Similarity	NPC471826
0.8382	Intermediate Similarity	NPC188327
0.838	Intermediate Similarity	NPC268081
0.8377	Intermediate Similarity	NPC14822
0.837	Intermediate Similarity	NPC291899
0.8369	Intermediate Similarity	NPC66705
0.8367	Intermediate Similarity	NPC469700
0.8367	Intermediate Similarity	NPC474302
0.8357	Intermediate Similarity	NPC141822
0.8357	Intermediate Similarity	NPC142563
0.8357	Intermediate Similarity	NPC241165
0.8357	Intermediate Similarity	NPC205797
0.8357	Intermediate Similarity	NPC1220
0.8357	Intermediate Similarity	NPC291551
0.8356	Intermediate Similarity	NPC226722

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 NPC471072 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	857
0.2-0.3	1750
0.3-0.4	2573
0.4-0.5	1945
0.5-0.6	1137
0.6-0.7	406
0.7-0.8	118
0.8-0.85	46
0.85-0.9	12
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8815	High Similarity	NPD6859	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD6799	Approved
0.8467	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD422	Phase 1
0.8357	Intermediate Similarity	NPD5124	Phase 1
0.8357	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1652	Phase 2
0.8301	Intermediate Similarity	NPD7075	Discontinued
0.8278	Intermediate Similarity	NPD6801	Discontinued
0.8273	Intermediate Similarity	NPD6798	Discontinued
0.8273	Intermediate Similarity	NPD1296	Phase 2
0.8267	Intermediate Similarity	NPD6599	Discontinued
0.8227	Intermediate Similarity	NPD6355	Discontinued
0.8188	Intermediate Similarity	NPD5403	Approved
0.8176	Intermediate Similarity	NPD5401	Approved
0.8175	Intermediate Similarity	NPD2797	Approved
0.8151	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD3750	Approved
0.8151	Intermediate Similarity	NPD4628	Phase 3
0.8125	Intermediate Similarity	NPD2796	Approved
0.8105	Intermediate Similarity	NPD7819	Suspended
0.8056	Intermediate Similarity	NPD3748	Approved
0.8014	Intermediate Similarity	NPD1549	Phase 2
0.8014	Intermediate Similarity	NPD3268	Approved
0.8	Intermediate Similarity	NPD7768	Phase 2
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6832	Phase 2
0.7974	Intermediate Similarity	NPD7411	Suspended
0.7959	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD6233	Phase 2
0.7949	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD3817	Phase 2
0.7931	Intermediate Similarity	NPD7033	Discontinued
0.7908	Intermediate Similarity	NPD4380	Phase 2
0.7877	Intermediate Similarity	NPD1551	Phase 2
0.7872	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD3225	Approved
0.7832	Intermediate Similarity	NPD4062	Phase 3
0.7826	Intermediate Similarity	NPD9717	Approved
0.7821	Intermediate Similarity	NPD5402	Approved
0.7815	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD1510	Phase 2
0.7808	Intermediate Similarity	NPD4308	Phase 3
0.7806	Intermediate Similarity	NPD1934	Approved
0.7786	Intermediate Similarity	NPD3266	Approved
0.7786	Intermediate Similarity	NPD3267	Approved
0.7785	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1240	Approved
0.7778	Intermediate Similarity	NPD1653	Approved
0.777	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD5844	Phase 1
0.773	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD1548	Phase 1
0.7718	Intermediate Similarity	NPD1243	Approved
0.7712	Intermediate Similarity	NPD920	Approved
0.7707	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1607	Approved
0.7669	Intermediate Similarity	NPD7843	Approved
0.766	Intermediate Similarity	NPD1203	Approved
0.7658	Intermediate Similarity	NPD3882	Suspended
0.7655	Intermediate Similarity	NPD4307	Phase 2
0.7651	Intermediate Similarity	NPD2424	Discontinued
0.7643	Intermediate Similarity	NPD8455	Phase 2
0.7643	Intermediate Similarity	NPD2801	Approved
0.7622	Intermediate Similarity	NPD4908	Phase 1
0.7619	Intermediate Similarity	NPD7097	Phase 1
0.7612	Intermediate Similarity	NPD1241	Discontinued
0.7591	Intermediate Similarity	NPD1894	Discontinued
0.7582	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7199	Phase 2
0.7569	Intermediate Similarity	NPD7095	Approved
0.7568	Intermediate Similarity	NPD2799	Discontinued
0.7562	Intermediate Similarity	NPD919	Approved
0.7561	Intermediate Similarity	NPD3818	Discontinued
0.7557	Intermediate Similarity	NPD1358	Approved
0.7546	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1613	Approved
0.7534	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6099	Approved
0.7517	Intermediate Similarity	NPD6100	Approved
0.7517	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2935	Discontinued
0.7516	Intermediate Similarity	NPD1511	Approved
0.7515	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD2684	Approved
0.75	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD3749	Approved
0.75	Intermediate Similarity	NPD1091	Approved
0.7485	Intermediate Similarity	NPD6559	Discontinued
0.7485	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4340	Discontinued
0.7483	Intermediate Similarity	NPD230	Phase 1
0.7483	Intermediate Similarity	NPD1019	Discontinued
0.7483	Intermediate Similarity	NPD447	Suspended
0.7482	Intermediate Similarity	NPD1778	Approved
0.747	Intermediate Similarity	NPD7472	Approved
0.747	Intermediate Similarity	NPD7074	Phase 3
0.7469	Intermediate Similarity	NPD8127	Discontinued
0.7467	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6002	Phase 3
0.7467	Intermediate Similarity	NPD6004	Phase 3
0.7467	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6005	Phase 3
0.7465	Intermediate Similarity	NPD8651	Approved
0.7464	Intermediate Similarity	NPD9545	Approved
0.7448	Intermediate Similarity	NPD3027	Phase 3
0.7447	Intermediate Similarity	NPD1608	Approved
0.744	Intermediate Similarity	NPD7808	Phase 3
0.7439	Intermediate Similarity	NPD6166	Phase 2
0.7439	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD290	Approved
0.7421	Intermediate Similarity	NPD1465	Phase 2
0.7419	Intermediate Similarity	NPD1512	Approved
0.7419	Intermediate Similarity	NPD5049	Phase 3
0.7419	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD4534	Discontinued
0.7415	Intermediate Similarity	NPD4060	Phase 1
0.7407	Intermediate Similarity	NPD5535	Approved
0.7405	Intermediate Similarity	NPD9697	Approved
0.7397	Intermediate Similarity	NPD2313	Discontinued
0.7386	Intermediate Similarity	NPD2354	Approved
0.7386	Intermediate Similarity	NPD3887	Approved
0.7381	Intermediate Similarity	NPD7251	Discontinued
0.7379	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4288	Approved
0.7372	Intermediate Similarity	NPD7157	Approved
0.7372	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1933	Approved
0.7365	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD5647	Approved
0.7358	Intermediate Similarity	NPD37	Approved
0.7355	Intermediate Similarity	NPD2533	Approved
0.7355	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2534	Approved
0.7355	Intermediate Similarity	NPD2532	Approved
0.7351	Intermediate Similarity	NPD5763	Approved
0.7351	Intermediate Similarity	NPD5762	Approved
0.7348	Intermediate Similarity	NPD3134	Approved
0.7346	Intermediate Similarity	NPD6234	Discontinued
0.7338	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4965	Approved
0.7329	Intermediate Similarity	NPD4967	Phase 2
0.7329	Intermediate Similarity	NPD4966	Approved
0.7321	Intermediate Similarity	NPD6797	Phase 2
0.732	Intermediate Similarity	NPD4110	Phase 3
0.732	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7229	Phase 3
0.7315	Intermediate Similarity	NPD6653	Approved
0.731	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3496	Discontinued
0.7305	Intermediate Similarity	NPD3847	Discontinued
0.7305	Intermediate Similarity	NPD7286	Phase 2
0.7303	Intermediate Similarity	NPD5958	Discontinued
0.7301	Intermediate Similarity	NPD5494	Approved
0.729	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2239	Approved
0.7285	Intermediate Similarity	NPD2240	Approved
0.7285	Intermediate Similarity	NPD4476	Approved
0.7285	Intermediate Similarity	NPD4477	Approved
0.7284	Intermediate Similarity	NPD6971	Discontinued
0.7279	Intermediate Similarity	NPD411	Approved
0.7279	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6190	Approved
0.7273	Intermediate Similarity	NPD4749	Approved
0.726	Intermediate Similarity	NPD2614	Approved
0.7254	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1535	Discovery
0.7234	Intermediate Similarity	NPD17	Approved
0.7219	Intermediate Similarity	NPD5953	Discontinued
0.7212	Intermediate Similarity	NPD6232	Discontinued
0.7203	Intermediate Similarity	NPD1481	Phase 2
0.72	Intermediate Similarity	NPD6651	Approved
0.7197	Intermediate Similarity	NPD6273	Approved
0.7194	Intermediate Similarity	NPD9493	Approved
0.7186	Intermediate Similarity	NPD7473	Discontinued
0.7172	Intermediate Similarity	NPD6362	Approved
0.7171	Intermediate Similarity	NPD6032	Approved
0.717	Intermediate Similarity	NPD7458	Discontinued
0.717	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5691	Approved
0.7162	Intermediate Similarity	NPD3764	Approved
0.7162	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD2800	Approved
0.7143	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD7549	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