NPASS Compound

Structure

NPC469469 OpenBabel07101718202D 36 36 0 0 1 0 0 0 0 0999 V2000 3.4641 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 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 6.0622 -0.5000 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 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 1.7321 1.0000 0.0000 C 0 0 0 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 3.4641 1.0000 0.0000 C 0 0 0 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 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 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 -2.5981 -0.5000 0.0000 O 0 0 0 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 2.5000 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 0.8660 1.5000 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 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 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 2 0 0 0 0 10 11 1 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 2 0 0 0 0 17 23 1 0 0 0 0 18 28 1 0 0 0 0 19 21 1 0 0 0 0 19 34 1 0 0 0 0 20 21 1 0 0 0 0 20 35 1 0 0 0 0 21 29 1 1 0 0 0 22 18 1 6 0 0 0 22 24 1 0 0 0 0 22 36 1 0 0 0 0 23 30 2 0 0 0 0 23 34 1 0 0 0 0 24 25 1 0 0 0 0 24 31 1 1 0 0 0 25 26 1 0 0 0 0 25 32 1 6 0 0 0 26 27 1 0 0 0 0 26 33 1 1 0 0 0 27 35 1 6 0 0 0 27 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.33
Volume:	538.194
LogP:	3.522
LogD:	3.094
LogS:	-3.91
# Rotatable Bonds:	21
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	1
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.094
Synthetic Accessibility Score:	4.243
Fsp3:	0.815
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:	-5.3
MDCK Permeability:	5.2337036322569475e-05
Pgp-inhibitor:	0.129
Pgp-substrate:	0.793
Human Intestinal Absorption (HIA):	0.536
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	97.0372085571289%
Volume Distribution (VD):	0.966
Pgp-substrate:	2.1992321014404297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.087
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.078
CYP2C9-substrate:	0.221
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.185
CYP3A4-substrate:	0.032

ADMET: Excretion

Clearance (CL):	3.851
Half-life (T1/2):	0.935

ADMET: Toxicity

hERG Blockers:	0.476
Human Hepatotoxicity (H-HT):	0.047
Drug-inuced Liver Injury (DILI):	0.006
AMES Toxicity:	0.424
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.954
Carcinogencity:	0.334
Eye Corrosion:	0.003
Eye Irritation:	0.044
Respiratory Toxicity:	0.082

Download Data

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

Natural Product: NPC469469

Natural Product ID:	NPC469469
*Common Name:**	(2S)-1-O-(9Z,12Z-Octadecadienoyl)-3-O-Beta-D-Galactopyranosylglycerol
IUPAC Name:	[(2S)-2-hydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] (2Z,9Z)-octadeca-2,9-dienoate
Synonyms:
Standard InCHIKey:	GGGMEAYBEYLYDS-QBICKONLSA-N
Standard InCHI:	InChI=1S/C27H48O9/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(30)34-19-21(29)20-35-27-26(33)25(32)24(31)22(18-28)36-27/h9-10,16-17,21-22,24-29,31-33H,2-8,11-15,18-20H2,1H3/b10-9-,17-16-/t21-,22-,24-,25+,26-,27-/m1/s1
SMILES:	CCCCCCCCC=CCCCCCC=CC(=O)OCC(COC1C(C(C(C(O1)CO)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079508
PubChem CID:	46882929
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000175] Glycerolipids [CHEMONTID:0000637] Glycosylglycerols [CHEMONTID:0003819] Glycosylmonoradylglycerols [CHEMONTID:0001773] Glycosylmonoacylglycerols

*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
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19739599]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24811	Cibotium barometz	Species	Cibotiaceae	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
Others	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	65.0	%	PMID[570412]
NPT2	Others	Unspecified		Inhibition	=	83.0	%	PMID[570412]

☑ 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 NPC469469 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	163
0.1-0.2	1936
0.2-0.3	6209
0.3-0.4	15149
0.4-0.5	11032
0.5-0.6	6245
0.6-0.7	1611
0.7-0.8	299
0.8-0.85	31
0.85-0.9	10
0.9-0.95	11
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC208473
0.9367	High Similarity	NPC473308
0.9359	High Similarity	NPC251026
0.9241	High Similarity	NPC142111
0.9241	High Similarity	NPC473315
0.9079	High Similarity	NPC326661
0.8929	High Similarity	NPC473311
0.8889	High Similarity	NPC266718
0.8824	High Similarity	NPC469410
0.8734	High Similarity	NPC180725
0.8718	High Similarity	NPC474026
0.869	High Similarity	NPC470137
0.8659	High Similarity	NPC475035
0.8625	High Similarity	NPC163362
0.8625	High Similarity	NPC127295
0.8625	High Similarity	NPC470147
0.8625	High Similarity	NPC133226
0.8608	High Similarity	NPC248775
0.8571	High Similarity	NPC475186
0.8571	High Similarity	NPC118077
0.8571	High Similarity	NPC475037
0.8554	High Similarity	NPC470124
0.8506	High Similarity	NPC472196
0.8506	High Similarity	NPC472195
0.8506	High Similarity	NPC238090
0.85	High Similarity	NPC470149
0.85	High Similarity	NPC470148
0.8409	Intermediate Similarity	NPC159698
0.8372	Intermediate Similarity	NPC285588
0.8333	Intermediate Similarity	NPC475034
0.8293	Intermediate Similarity	NPC21693
0.8293	Intermediate Similarity	NPC236649
0.8276	Intermediate Similarity	NPC118078
0.8276	Intermediate Similarity	NPC202886
0.825	Intermediate Similarity	NPC110813
0.8228	Intermediate Similarity	NPC285840
0.8228	Intermediate Similarity	NPC327041
0.8205	Intermediate Similarity	NPC327383
0.8205	Intermediate Similarity	NPC185186
0.8182	Intermediate Similarity	NPC110072
0.8182	Intermediate Similarity	NPC477749
0.8182	Intermediate Similarity	NPC474078
0.8161	Intermediate Similarity	NPC477748
0.8148	Intermediate Similarity	NPC133377
0.8101	Intermediate Similarity	NPC472174
0.8101	Intermediate Similarity	NPC472173
0.8095	Intermediate Similarity	NPC156089
0.8095	Intermediate Similarity	NPC473500
0.8095	Intermediate Similarity	NPC470313
0.8095	Intermediate Similarity	NPC38295
0.8077	Intermediate Similarity	NPC475762
0.8065	Intermediate Similarity	NPC2313
0.8065	Intermediate Similarity	NPC471637
0.8065	Intermediate Similarity	NPC154132
0.8065	Intermediate Similarity	NPC475157
0.8065	Intermediate Similarity	NPC57586
0.8065	Intermediate Similarity	NPC475655
0.8049	Intermediate Similarity	NPC1180
0.8025	Intermediate Similarity	NPC475711
0.8	Intermediate Similarity	NPC256368
0.8	Intermediate Similarity	NPC294293
0.8	Intermediate Similarity	NPC288471
0.7975	Intermediate Similarity	NPC329914
0.7975	Intermediate Similarity	NPC55652
0.7975	Intermediate Similarity	NPC132938
0.7949	Intermediate Similarity	NPC476012
0.7927	Intermediate Similarity	NPC477314
0.7907	Intermediate Similarity	NPC471494
0.7901	Intermediate Similarity	NPC229655
0.7895	Intermediate Similarity	NPC197736
0.7889	Intermediate Similarity	NPC320089
0.7865	Intermediate Similarity	NPC303451
0.7865	Intermediate Similarity	NPC327253
0.7865	Intermediate Similarity	NPC471569
0.7865	Intermediate Similarity	NPC6414
0.7857	Intermediate Similarity	NPC280367
0.7831	Intermediate Similarity	NPC179933
0.7816	Intermediate Similarity	NPC311163
0.7805	Intermediate Similarity	NPC233071
0.7789	Intermediate Similarity	NPC201191
0.775	Intermediate Similarity	NPC329890
0.7732	Intermediate Similarity	NPC315070
0.7722	Intermediate Similarity	NPC476037
0.7717	Intermediate Similarity	NPC469543
0.7692	Intermediate Similarity	NPC320552
0.7692	Intermediate Similarity	NPC61201
0.7692	Intermediate Similarity	NPC475760
0.7684	Intermediate Similarity	NPC198992
0.7683	Intermediate Similarity	NPC188860
0.7674	Intermediate Similarity	NPC263087
0.7674	Intermediate Similarity	NPC31019
0.7674	Intermediate Similarity	NPC27314
0.7674	Intermediate Similarity	NPC106912
0.7674	Intermediate Similarity	NPC2379
0.7667	Intermediate Similarity	NPC177668
0.7634	Intermediate Similarity	NPC173329
0.7634	Intermediate Similarity	NPC306041
0.7634	Intermediate Similarity	NPC288350
0.7632	Intermediate Similarity	NPC294813
0.7632	Intermediate Similarity	NPC13143
0.7619	Intermediate Similarity	NPC139712
0.7619	Intermediate Similarity	NPC321728
0.7614	Intermediate Similarity	NPC47937
0.7582	Intermediate Similarity	NPC477349
0.7582	Intermediate Similarity	NPC472197
0.7582	Intermediate Similarity	NPC472199
0.7556	Intermediate Similarity	NPC133450
0.7553	Intermediate Similarity	NPC476612
0.7553	Intermediate Similarity	NPC476613
0.7553	Intermediate Similarity	NPC472290
0.7551	Intermediate Similarity	NPC239961
0.7532	Intermediate Similarity	NPC19769
0.7528	Intermediate Similarity	NPC313658
0.7528	Intermediate Similarity	NPC316138
0.7527	Intermediate Similarity	NPC170204
0.75	Intermediate Similarity	NPC329838
0.75	Intermediate Similarity	NPC475173
0.75	Intermediate Similarity	NPC133625
0.75	Intermediate Similarity	NPC182383
0.75	Intermediate Similarity	NPC473663
0.75	Intermediate Similarity	NPC329615
0.75	Intermediate Similarity	NPC477014
0.75	Intermediate Similarity	NPC322529
0.75	Intermediate Similarity	NPC120398
0.75	Intermediate Similarity	NPC477013
0.75	Intermediate Similarity	NPC473723
0.75	Intermediate Similarity	NPC471567
0.75	Intermediate Similarity	NPC473561
0.75	Intermediate Similarity	NPC473520
0.7474	Intermediate Similarity	NPC40182
0.7474	Intermediate Similarity	NPC198422
0.7474	Intermediate Similarity	NPC203627
0.7474	Intermediate Similarity	NPC472015
0.7473	Intermediate Similarity	NPC473904
0.7473	Intermediate Similarity	NPC3952
0.7471	Intermediate Similarity	NPC229799
0.7471	Intermediate Similarity	NPC286770
0.7471	Intermediate Similarity	NPC284472
0.7447	Intermediate Similarity	NPC143446
0.7447	Intermediate Similarity	NPC54731
0.7444	Intermediate Similarity	NPC320458
0.7444	Intermediate Similarity	NPC280621
0.7444	Intermediate Similarity	NPC89001
0.7444	Intermediate Similarity	NPC233551
0.7444	Intermediate Similarity	NPC48338
0.7444	Intermediate Similarity	NPC473905
0.7444	Intermediate Similarity	NPC21208
0.7444	Intermediate Similarity	NPC20339
0.7444	Intermediate Similarity	NPC40376
0.7442	Intermediate Similarity	NPC473339
0.7442	Intermediate Similarity	NPC184208
0.7442	Intermediate Similarity	NPC471552
0.7442	Intermediate Similarity	NPC8538
0.7439	Intermediate Similarity	NPC477312
0.7439	Intermediate Similarity	NPC477313
0.7439	Intermediate Similarity	NPC477315
0.7439	Intermediate Similarity	NPC477304
0.7439	Intermediate Similarity	NPC477308
0.7439	Intermediate Similarity	NPC477309
0.7439	Intermediate Similarity	NPC477316
0.7439	Intermediate Similarity	NPC477305
0.7436	Intermediate Similarity	NPC201356
0.7436	Intermediate Similarity	NPC276299
0.7419	Intermediate Similarity	NPC163409
0.7419	Intermediate Similarity	NPC44682
0.7419	Intermediate Similarity	NPC472198
0.7419	Intermediate Similarity	NPC25701
0.7419	Intermediate Similarity	NPC477348
0.7419	Intermediate Similarity	NPC2003
0.7419	Intermediate Similarity	NPC477345
0.7419	Intermediate Similarity	NPC238264
0.7416	Intermediate Similarity	NPC477015
0.7412	Intermediate Similarity	NPC473947
0.7403	Intermediate Similarity	NPC31496
0.7403	Intermediate Similarity	NPC148233
0.7403	Intermediate Similarity	NPC25747
0.74	Intermediate Similarity	NPC177524
0.74	Intermediate Similarity	NPC219900
0.74	Intermediate Similarity	NPC392
0.7396	Intermediate Similarity	NPC130792
0.7391	Intermediate Similarity	NPC9447
0.7391	Intermediate Similarity	NPC473707
0.7386	Intermediate Similarity	NPC156804
0.7386	Intermediate Similarity	NPC163093
0.7381	Intermediate Similarity	NPC477203
0.7374	Intermediate Similarity	NPC82251
0.7368	Intermediate Similarity	NPC309503
0.7368	Intermediate Similarity	NPC91197
0.7368	Intermediate Similarity	NPC155319
0.7368	Intermediate Similarity	NPC475332
0.7368	Intermediate Similarity	NPC96597
0.7368	Intermediate Similarity	NPC40812
0.7368	Intermediate Similarity	NPC26810
0.7368	Intermediate Similarity	NPC239547
0.7368	Intermediate Similarity	NPC125551
0.7363	Intermediate Similarity	NPC139418
0.7363	Intermediate Similarity	NPC477016
0.7363	Intermediate Similarity	NPC477017
0.7356	Intermediate Similarity	NPC310450
0.7356	Intermediate Similarity	NPC11383

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 NPC469469 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	2366
0.2-0.3	4056
0.3-0.4	1844
0.4-0.5	553
0.5-0.6	166
0.6-0.7	19
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7474	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD6698	Approved
0.7473	Intermediate Similarity	NPD46	Approved
0.7473	Intermediate Similarity	NPD7838	Discovery
0.74	Intermediate Similarity	NPD6686	Approved
0.7097	Intermediate Similarity	NPD8522	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5344	Discontinued
0.6757	Remote Similarity	NPD7503	Approved
0.6637	Remote Similarity	NPD7829	Approved
0.6637	Remote Similarity	NPD7830	Approved
0.6636	Remote Similarity	NPD7327	Approved
0.6636	Remote Similarity	NPD7328	Approved
0.6577	Remote Similarity	NPD7516	Approved
0.6542	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD8377	Approved
0.6518	Remote Similarity	NPD8294	Approved
0.6495	Remote Similarity	NPD7983	Approved
0.6491	Remote Similarity	NPD7642	Approved
0.646	Remote Similarity	NPD8296	Approved
0.646	Remote Similarity	NPD8380	Approved
0.646	Remote Similarity	NPD8033	Approved
0.646	Remote Similarity	NPD8335	Approved
0.646	Remote Similarity	NPD8379	Approved
0.646	Remote Similarity	NPD8378	Approved
0.64	Remote Similarity	NPD2269	Approved
0.6373	Remote Similarity	NPD6648	Approved
0.6346	Remote Similarity	NPD1407	Approved
0.6339	Remote Similarity	NPD7641	Discontinued
0.6316	Remote Similarity	NPD8515	Approved
0.6316	Remote Similarity	NPD8513	Phase 3
0.6316	Remote Similarity	NPD8444	Approved
0.6316	Remote Similarity	NPD8516	Approved
0.6316	Remote Similarity	NPD8517	Approved
0.6267	Remote Similarity	NPD904	Phase 3
0.6267	Remote Similarity	NPD905	Approved
0.6239	Remote Similarity	NPD7507	Approved
0.6173	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD6412	Phase 2
0.6168	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD3197	Phase 1
0.6125	Remote Similarity	NPD6109	Phase 1
0.6118	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD887	Approved
0.6104	Remote Similarity	NPD895	Approved
0.6104	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD889	Approved
0.6104	Remote Similarity	NPD892	Phase 3
0.6104	Remote Similarity	NPD888	Phase 3
0.6104	Remote Similarity	NPD894	Approved
0.6104	Remote Similarity	NPD891	Phase 3
0.6104	Remote Similarity	NPD893	Approved
0.6102	Remote Similarity	NPD8451	Approved
0.6083	Remote Similarity	NPD7319	Approved
0.6082	Remote Similarity	NPD4250	Approved
0.6082	Remote Similarity	NPD4251	Approved
0.6078	Remote Similarity	NPD7839	Suspended
0.6071	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.605	Remote Similarity	NPD8448	Approved
0.6022	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6371	Approved
0.5979	Remote Similarity	NPD4249	Approved
0.5976	Remote Similarity	NPD6123	Approved
0.5962	Remote Similarity	NPD4225	Approved
0.593	Remote Similarity	NPD896	Approved
0.593	Remote Similarity	NPD897	Approved
0.593	Remote Similarity	NPD898	Approved
0.5926	Remote Similarity	NPD69	Approved
0.5926	Remote Similarity	NPD9119	Approved
0.5926	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD8391	Approved
0.5902	Remote Similarity	NPD8390	Approved
0.5902	Remote Similarity	NPD8392	Approved
0.5882	Remote Similarity	NPD8342	Approved
0.5882	Remote Similarity	NPD8341	Approved
0.5882	Remote Similarity	NPD8340	Approved
0.5882	Remote Similarity	NPD8299	Approved
0.5875	Remote Similarity	NPD2267	Suspended
0.5841	Remote Similarity	NPD8133	Approved
0.5833	Remote Similarity	NPD6110	Phase 1
0.581	Remote Similarity	NPD7638	Approved
0.5806	Remote Similarity	NPD4271	Approved
0.5806	Remote Similarity	NPD4268	Approved
0.5802	Remote Similarity	NPD9118	Approved
0.5798	Remote Similarity	NPD8328	Phase 3
0.5785	Remote Similarity	NPD8074	Phase 3
0.578	Remote Similarity	NPD4211	Phase 1
0.5769	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD7640	Approved
0.5755	Remote Similarity	NPD7639	Approved
0.5748	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD7329	Approved
0.5743	Remote Similarity	NPD5785	Approved
0.573	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD7266	Discontinued
0.5714	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.569	Remote Similarity	NPD7505	Discontinued
0.5686	Remote Similarity	NPD7637	Suspended
0.5684	Remote Similarity	NPD4820	Approved
0.5684	Remote Similarity	NPD4821	Approved
0.5684	Remote Similarity	NPD4819	Approved
0.5684	Remote Similarity	NPD4822	Approved
0.567	Remote Similarity	NPD7154	Phase 3
0.5631	Remote Similarity	NPD5779	Approved
0.5631	Remote Similarity	NPD5778	Approved
0.5625	Remote Similarity	NPD7346	Approved
0.5614	Remote Similarity	NPD6429	Approved
0.5614	Remote Similarity	NPD6430	Approved
0.5604	Remote Similarity	NPD3181	Approved
0.56	Remote Similarity	NPD8998	Phase 2
0.56	Remote Similarity	NPD8993	Phase 1
0.56	Remote Similarity	NPD8999	Phase 3
0.56	Remote Similarity	NPD8997	Approved
0.56	Remote Similarity	NPD9000	Phase 3

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