NPASS Compound

Structure

NPC268930 OpenBabel07101719512D 42 45 0 0 1 0 0 0 0 0999 V2000 -2.1183 -1.7562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9647 -3.2221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3824 -4.4816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2678 -4.1050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6176 3.2810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0164 4.9260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4533 1.5332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9419 0.6869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8323 -1.4508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1204 -0.5169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6091 -0.0040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7628 -0.4926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6091 0.9732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9165 -0.0040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7628 1.4618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8110 -1.7562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8835 -2.8642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8110 -0.7790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1671 -2.1995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2416 3.7581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7926 1.8829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1183 -0.7790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1044 -1.0247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9647 -2.2448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6660 -3.8169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2919 3.9883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9165 0.9732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9647 -0.2903 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3846 -1.2468 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7761 0.9732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0702 1.4618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3985 1.3976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7198 0.2220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2720 0.6869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9647 0.6869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1676 -0.7344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2720 -0.2903 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1183 1.1755 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0702 2.4391 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2529 2.3639 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4257 1.1755 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 24 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 26 1 0 0 0 0 7 35 1 0 0 0 0 8 35 1 0 0 0 0 9 36 1 0 0 0 0 10 36 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 2 0 0 0 0 14 27 2 0 0 0 0 15 27 1 0 0 0 0 16 18 1 0 0 0 0 16 24 2 0 0 0 0 17 19 1 0 0 0 0 17 25 2 0 0 0 0 20 21 1 0 0 0 0 20 26 2 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 23 37 1 0 0 0 0 27 31 1 0 0 0 0 28 18 1 1 0 0 0 28 35 1 0 0 0 0 29 19 1 1 0 0 0 29 36 1 0 0 0 0 30 31 1 0 0 0 0 30 32 1 0 0 0 0 30 33 2 0 0 0 0 31 39 2 0 0 0 0 32 38 1 0 0 0 0 32 40 2 0 0 0 0 33 37 1 0 0 0 0 33 42 1 0 0 0 0 34 37 1 0 0 0 0 34 38 1 0 0 0 0 34 41 2 0 0 0 0 35 38 1 0 0 0 0 36 42 1 0 0 0 0 37 22 1 1 0 0 0 38 21 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	570.37
Volume:	640.374
LogP:	9.392
LogD:	6.283
LogS:	-5.691
# Rotatable Bonds:	8
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.135
Synthetic Accessibility Score:	5.961
Fsp3:	0.553
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.97
MDCK Permeability:	1.4290342733147554e-05
Pgp-inhibitor:	0.359
Pgp-substrate:	0.076
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.929
30% Bioavailability (F30%):	0.943

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	95.00055694580078%
Volume Distribution (VD):	2.681
Pgp-substrate:	6.302977561950684%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.143
CYP2C19-inhibitor:	0.704
CYP2C19-substrate:	0.731
CYP2C9-inhibitor:	0.929
CYP2C9-substrate:	0.158
CYP2D6-inhibitor:	0.52
CYP2D6-substrate:	0.01
CYP3A4-inhibitor:	0.914
CYP3A4-substrate:	0.847

ADMET: Excretion

Clearance (CL):	10.244
Half-life (T1/2):	0.007

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.972
Drug-inuced Liver Injury (DILI):	0.857
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.545
Maximum Recommended Daily Dose:	0.871
Skin Sensitization:	0.072
Carcinogencity:	0.255
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC268930

Natural Product ID:	NPC268930
*Common Name:**	MRATVVGQUZRDNO-DORJWPPLSA-N
IUPAC Name:	n.a.
Synonyms:	13,14-Didehydoxyisogarcinol
Standard InCHIKey:	MRATVVGQUZRDNO-DORJWPPLSA-N
Standard InCHI:	InChI=1S/C38H50O4/c1-24(2)16-18-28-22-37-23-29(19-17-25(3)4)36(9,10)42-33(37)30(31(39)27-14-12-11-13-15-27)32(40)38(34(37)41,35(28,7)8)21-20-26(5)6/h11-17,20,28-29H,18-19,21-23H2,1-10H3/t28-,29+,37+,38+/m1/s1
SMILES:	CC(=CC[C@]12C(=O)C(=C3[C@@](C1=O)(C[C@@H](C(O3)(C)C)CC=C(C)C)C[C@H](C2(C)C)CC=C(C)C)C(=O)c1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL554161
PubChem CID:	25243255
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO33077	garcinina multiflora	Species	n.a.	n.a.	fruits	n.a.	n.a.	PMID[19203247]

☑ 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

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	880.0	nM	PMID[485820]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1160.0	nM	PMID[485820]

☑ 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 NPC268930 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	338
0.1-0.2	1370
0.2-0.3	2476
0.3-0.4	8137
0.4-0.5	14544
0.5-0.6	12970
0.6-0.7	2609
0.7-0.8	204
0.8-0.85	27
0.85-0.9	18
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9817	High Similarity	NPC260886
0.9217	High Similarity	NPC476225
0.9107	High Similarity	NPC130591
0.9107	High Similarity	NPC234637
0.9018	High Similarity	NPC471481
0.8957	High Similarity	NPC61651
0.8929	High Similarity	NPC218855
0.8908	High Similarity	NPC325740
0.877	High Similarity	NPC316553
0.8607	High Similarity	NPC294050
0.8607	High Similarity	NPC328997
0.8537	High Similarity	NPC146239
0.8525	High Similarity	NPC472693
0.8525	High Similarity	NPC472694
0.8448	Intermediate Similarity	NPC294458
0.8403	Intermediate Similarity	NPC472697
0.8403	Intermediate Similarity	NPC472698
0.8378	Intermediate Similarity	NPC474866
0.8378	Intermediate Similarity	NPC472691
0.8378	Intermediate Similarity	NPC471829
0.8378	Intermediate Similarity	NPC475939
0.824	Intermediate Similarity	NPC470648
0.8226	Intermediate Similarity	NPC478108
0.8197	Intermediate Similarity	NPC476234
0.8175	Intermediate Similarity	NPC472678
0.8145	Intermediate Similarity	NPC472681
0.814	Intermediate Similarity	NPC144257
0.8125	Intermediate Similarity	NPC471334
0.8125	Intermediate Similarity	NPC472692
0.8125	Intermediate Similarity	NPC472682
0.812	Intermediate Similarity	NPC280789
0.8106	Intermediate Similarity	NPC118366
0.8095	Intermediate Similarity	NPC48992
0.8087	Intermediate Similarity	NPC470007
0.8067	Intermediate Similarity	NPC215419
0.8051	Intermediate Similarity	NPC477476
0.8051	Intermediate Similarity	NPC477475
0.8047	Intermediate Similarity	NPC471832
0.8017	Intermediate Similarity	NPC94425
0.7983	Intermediate Similarity	NPC326664
0.7967	Intermediate Similarity	NPC472679
0.7967	Intermediate Similarity	NPC472680
0.7956	Intermediate Similarity	NPC469375
0.7956	Intermediate Similarity	NPC8493
0.7956	Intermediate Similarity	NPC294679
0.7956	Intermediate Similarity	NPC144247
0.7956	Intermediate Similarity	NPC145301
0.7946	Intermediate Similarity	NPC54647
0.7931	Intermediate Similarity	NPC472696
0.7931	Intermediate Similarity	NPC472683
0.7931	Intermediate Similarity	NPC472701
0.7931	Intermediate Similarity	NPC472695
0.7907	Intermediate Similarity	NPC25736
0.7899	Intermediate Similarity	NPC93287
0.7876	Intermediate Similarity	NPC109514
0.7863	Intermediate Similarity	NPC192577
0.7857	Intermediate Similarity	NPC328107
0.7845	Intermediate Similarity	NPC472699
0.7845	Intermediate Similarity	NPC472700
0.7823	Intermediate Similarity	NPC474222
0.7823	Intermediate Similarity	NPC475804
0.7787	Intermediate Similarity	NPC469843
0.7768	Intermediate Similarity	NPC239185
0.7752	Intermediate Similarity	NPC268607
0.775	Intermediate Similarity	NPC470253
0.775	Intermediate Similarity	NPC143768
0.7742	Intermediate Similarity	NPC202015
0.7739	Intermediate Similarity	NPC247976
0.7734	Intermediate Similarity	NPC470649
0.7734	Intermediate Similarity	NPC478107
0.7731	Intermediate Similarity	NPC137315
0.7731	Intermediate Similarity	NPC265513
0.7719	Intermediate Similarity	NPC476993
0.7717	Intermediate Similarity	NPC51079
0.7717	Intermediate Similarity	NPC85511
0.7712	Intermediate Similarity	NPC470252
0.7699	Intermediate Similarity	NPC134882
0.7698	Intermediate Similarity	NPC167323
0.7698	Intermediate Similarity	NPC269923
0.7692	Intermediate Similarity	NPC100767
0.7686	Intermediate Similarity	NPC471721
0.768	Intermediate Similarity	NPC475827
0.768	Intermediate Similarity	NPC474223
0.768	Intermediate Similarity	NPC232958
0.7674	Intermediate Similarity	NPC474106
0.7667	Intermediate Similarity	NPC292834
0.7638	Intermediate Similarity	NPC474159
0.7638	Intermediate Similarity	NPC474254
0.7632	Intermediate Similarity	NPC476042
0.7611	Intermediate Similarity	NPC265220
0.7606	Intermediate Similarity	NPC264229
0.7606	Intermediate Similarity	NPC46549
0.7591	Intermediate Similarity	NPC294330
0.7581	Intermediate Similarity	NPC323440
0.7581	Intermediate Similarity	NPC222968
0.7581	Intermediate Similarity	NPC80605
0.7578	Intermediate Similarity	NPC318067
0.7568	Intermediate Similarity	NPC1682
0.7568	Intermediate Similarity	NPC188844
0.7568	Intermediate Similarity	NPC59677
0.7544	Intermediate Similarity	NPC75724
0.7544	Intermediate Similarity	NPC145052
0.7541	Intermediate Similarity	NPC241851
0.7541	Intermediate Similarity	NPC67377
0.754	Intermediate Similarity	NPC238861
0.754	Intermediate Similarity	NPC77000
0.7522	Intermediate Similarity	NPC219573
0.7522	Intermediate Similarity	NPC185208
0.7521	Intermediate Similarity	NPC329282
0.7521	Intermediate Similarity	NPC212415
0.7518	Intermediate Similarity	NPC51531
0.7518	Intermediate Similarity	NPC469857
0.7518	Intermediate Similarity	NPC165191
0.7518	Intermediate Similarity	NPC5014
0.7518	Intermediate Similarity	NPC149773
0.7518	Intermediate Similarity	NPC245760
0.7518	Intermediate Similarity	NPC28592
0.7518	Intermediate Similarity	NPC91887
0.7518	Intermediate Similarity	NPC157284
0.7518	Intermediate Similarity	NPC50615
0.7518	Intermediate Similarity	NPC297797
0.7518	Intermediate Similarity	NPC473779
0.7518	Intermediate Similarity	NPC23667
0.7518	Intermediate Similarity	NPC42384
0.7518	Intermediate Similarity	NPC46242
0.7518	Intermediate Similarity	NPC473479
0.7518	Intermediate Similarity	NPC477849
0.7518	Intermediate Similarity	NPC114333
0.7518	Intermediate Similarity	NPC289358
0.75	Intermediate Similarity	NPC65627
0.7483	Intermediate Similarity	NPC132810
0.7481	Intermediate Similarity	NPC115797
0.7481	Intermediate Similarity	NPC51448
0.748	Intermediate Similarity	NPC474095
0.7479	Intermediate Similarity	NPC203732
0.7477	Intermediate Similarity	NPC284475
0.7466	Intermediate Similarity	NPC305710
0.7456	Intermediate Similarity	NPC240042
0.744	Intermediate Similarity	NPC152812
0.7438	Intermediate Similarity	NPC291799
0.7434	Intermediate Similarity	NPC260233
0.7419	Intermediate Similarity	NPC135730
0.7419	Intermediate Similarity	NPC62138
0.7411	Intermediate Similarity	NPC153885
0.7411	Intermediate Similarity	NPC323420
0.741	Intermediate Similarity	NPC473527
0.7398	Intermediate Similarity	NPC196075
0.7395	Intermediate Similarity	NPC85560
0.7395	Intermediate Similarity	NPC244933
0.7391	Intermediate Similarity	NPC49994
0.7381	Intermediate Similarity	NPC318173
0.7372	Intermediate Similarity	NPC7464
0.7348	Intermediate Similarity	NPC478162
0.7348	Intermediate Similarity	NPC478165
0.7345	Intermediate Similarity	NPC238219
0.7344	Intermediate Similarity	NPC472981
0.7344	Intermediate Similarity	NPC144547
0.7343	Intermediate Similarity	NPC471970
0.7343	Intermediate Similarity	NPC273798
0.7333	Intermediate Similarity	NPC472656
0.7328	Intermediate Similarity	NPC470765
0.7324	Intermediate Similarity	NPC469856
0.7324	Intermediate Similarity	NPC469854
0.7323	Intermediate Similarity	NPC204784
0.7321	Intermediate Similarity	NPC133461
0.7317	Intermediate Similarity	NPC469547
0.7305	Intermediate Similarity	NPC471971
0.7305	Intermediate Similarity	NPC471972
0.7305	Intermediate Similarity	NPC469855
0.7305	Intermediate Similarity	NPC30846
0.7304	Intermediate Similarity	NPC103048
0.7304	Intermediate Similarity	NPC278228
0.7288	Intermediate Similarity	NPC274443
0.728	Intermediate Similarity	NPC226093
0.7273	Intermediate Similarity	NPC470753
0.7273	Intermediate Similarity	NPC473220
0.7273	Intermediate Similarity	NPC51292
0.7266	Intermediate Similarity	NPC469680
0.7266	Intermediate Similarity	NPC289432
0.7266	Intermediate Similarity	NPC469681
0.7266	Intermediate Similarity	NPC988
0.7266	Intermediate Similarity	NPC105709
0.7266	Intermediate Similarity	NPC471974
0.7265	Intermediate Similarity	NPC112552
0.7257	Intermediate Similarity	NPC155232
0.7252	Intermediate Similarity	NPC295664
0.7241	Intermediate Similarity	NPC271475
0.7241	Intermediate Similarity	NPC476120
0.7239	Intermediate Similarity	NPC262819
0.7236	Intermediate Similarity	NPC474689
0.7236	Intermediate Similarity	NPC186128
0.7226	Intermediate Similarity	NPC474659
0.7226	Intermediate Similarity	NPC23894
0.7217	Intermediate Similarity	NPC12695
0.7207	Intermediate Similarity	NPC157778
0.7203	Intermediate Similarity	NPC222390
0.7203	Intermediate Similarity	NPC244427
0.72	Intermediate Similarity	NPC470764
0.72	Intermediate Similarity	NPC217111
0.72	Intermediate Similarity	NPC228936

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 NPC268930 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	876
0.2-0.3	1343
0.3-0.4	3298
0.4-0.5	2249
0.5-0.6	954
0.6-0.7	94
0.7-0.8	10
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
0.7768	Intermediate Similarity	NPD3495	Discontinued
0.776	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD7094	Approved
0.7603	Intermediate Similarity	NPD6858	Approved
0.7581	Intermediate Similarity	NPD7610	Discontinued
0.7568	Intermediate Similarity	NPD7631	Approved
0.754	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD7009	Phase 2
0.7477	Intermediate Similarity	NPD7609	Phase 3
0.7438	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD7961	Discontinued
0.7143	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1929	Approved
0.7143	Intermediate Similarity	NPD1930	Approved
0.7117	Intermediate Similarity	NPD650	Approved
0.7043	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2066	Phase 3
0.7008	Intermediate Similarity	NPD3317	Approved
0.6992	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3972	Approved
0.6947	Remote Similarity	NPD4879	Approved
0.6942	Remote Similarity	NPD5909	Discontinued
0.6929	Remote Similarity	NPD5951	Approved
0.6917	Remote Similarity	NPD1932	Approved
0.6897	Remote Similarity	NPD7236	Approved
0.687	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2329	Discontinued
0.6838	Remote Similarity	NPD7084	Phase 3
0.681	Remote Similarity	NPD1508	Approved
0.6788	Remote Similarity	NPD7055	Discontinued
0.6783	Remote Similarity	NPD1471	Phase 3
0.6727	Remote Similarity	NPD942	Approved
0.6719	Remote Similarity	NPD6010	Discontinued
0.6716	Remote Similarity	NPD4878	Approved
0.6667	Remote Similarity	NPD7239	Suspended
0.6643	Remote Similarity	NPD7713	Phase 3
0.6642	Remote Similarity	NPD2798	Approved
0.6642	Remote Similarity	NPD6287	Discontinued
0.6639	Remote Similarity	NPD1843	Approved
0.6639	Remote Similarity	NPD1989	Approved
0.6619	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7798	Approved
0.6552	Remote Similarity	NPD2346	Discontinued
0.6541	Remote Similarity	NPD3024	Approved
0.6541	Remote Similarity	NPD3025	Approved
0.6535	Remote Similarity	NPD1317	Discontinued
0.6531	Remote Similarity	NPD8166	Discontinued
0.6525	Remote Similarity	NPD1088	Approved
0.6522	Remote Similarity	NPD3573	Approved
0.6522	Remote Similarity	NPD1087	Approved
0.6516	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7008	Discontinued
0.6496	Remote Similarity	NPD1876	Approved
0.6496	Remote Similarity	NPD3673	Approved
0.6496	Remote Similarity	NPD3672	Approved
0.6493	Remote Similarity	NPD2932	Approved
0.6484	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6637	Approved
0.6457	Remote Similarity	NPD2182	Approved
0.6454	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6647	Phase 2
0.6449	Remote Similarity	NPD1470	Approved
0.6444	Remote Similarity	NPD3023	Approved
0.6444	Remote Similarity	NPD3026	Approved
0.6438	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD1693	Approved
0.6414	Remote Similarity	NPD2799	Discontinued
0.6408	Remote Similarity	NPD8032	Phase 2
0.6405	Remote Similarity	NPD7458	Discontinued
0.6397	Remote Similarity	NPD1201	Approved
0.6397	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD2193	Phase 2
0.6371	Remote Similarity	NPD2648	Phase 3
0.637	Remote Similarity	NPD3019	Approved
0.6356	Remote Similarity	NPD1089	Approved
0.6356	Remote Similarity	NPD1090	Approved
0.6356	Remote Similarity	NPD1086	Approved
0.6346	Remote Similarity	NPD7819	Suspended
0.6339	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD2313	Discontinued
0.6333	Remote Similarity	NPD1563	Approved
0.6333	Remote Similarity	NPD1202	Approved
0.6333	Remote Similarity	NPD3300	Phase 2
0.6331	Remote Similarity	NPD3267	Approved
0.6331	Remote Similarity	NPD3266	Approved
0.6319	Remote Similarity	NPD7799	Discontinued
0.6309	Remote Similarity	NPD7003	Approved
0.6301	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD3226	Approved
0.6288	Remote Similarity	NPD2629	Approved
0.6288	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5347	Phase 2
0.6271	Remote Similarity	NPD5346	Phase 2
0.6271	Remote Similarity	NPD800	Approved
0.627	Remote Similarity	NPD1237	Approved
0.627	Remote Similarity	NPD164	Approved
0.6266	Remote Similarity	NPD7058	Phase 2
0.6266	Remote Similarity	NPD7057	Phase 3
0.6259	Remote Similarity	NPD6099	Approved
0.6259	Remote Similarity	NPD6100	Approved
0.6259	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD2796	Approved
0.6258	Remote Similarity	NPD6585	Discontinued
0.625	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2345	Approved
0.625	Remote Similarity	NPD5836	Discontinued
0.6242	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD3268	Approved
0.622	Remote Similarity	NPD5048	Discontinued
0.6218	Remote Similarity	NPD7411	Suspended
0.6216	Remote Similarity	NPD2344	Approved
0.621	Remote Similarity	NPD1238	Approved
0.6209	Remote Similarity	NPD6273	Approved
0.62	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7487	Discontinued
0.62	Remote Similarity	NPD4628	Phase 3
0.6197	Remote Similarity	NPD6832	Phase 2
0.6194	Remote Similarity	NPD405	Clinical (unspecified phase)
0.619	Remote Similarity	NPD3748	Approved
0.619	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD7478	Approved
0.6184	Remote Similarity	NPD3950	Discontinued
0.6181	Remote Similarity	NPD7715	Approved
0.6181	Remote Similarity	NPD7714	Approved
0.6179	Remote Similarity	NPD1565	Approved
0.6179	Remote Similarity	NPD1566	Phase 3
0.6179	Remote Similarity	NPD1564	Approved
0.6176	Remote Similarity	NPD8434	Phase 2
0.6167	Remote Similarity	NPD1239	Approved
0.6165	Remote Similarity	NPD4766	Approved
0.6161	Remote Similarity	NPD227	Approved
0.6161	Remote Similarity	NPD225	Approved
0.616	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD2067	Discontinued
0.6154	Remote Similarity	NPD6039	Approved
0.6149	Remote Similarity	NPD5408	Approved
0.6149	Remote Similarity	NPD5404	Approved
0.6149	Remote Similarity	NPD5406	Approved
0.6149	Remote Similarity	NPD5405	Approved
0.6148	Remote Similarity	NPD6049	Phase 2
0.6148	Remote Similarity	NPD4094	Approved
0.6148	Remote Similarity	NPD6065	Approved
0.6148	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD4307	Phase 2
0.6115	Remote Similarity	NPD5890	Approved
0.6115	Remote Similarity	NPD5889	Approved
0.6111	Remote Similarity	NPD6024	Approved
0.6111	Remote Similarity	NPD2171	Approved
0.6111	Remote Similarity	NPD3764	Approved
0.6111	Remote Similarity	NPD6027	Approved
0.6111	Remote Similarity	NPD2196	Discontinued
0.6102	Remote Similarity	NPD4793	Discontinued
0.6102	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.609	Remote Similarity	NPD1241	Discontinued
0.609	Remote Similarity	NPD2650	Approved
0.609	Remote Similarity	NPD2652	Approved
0.6087	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD7305	Phase 1
0.6078	Remote Similarity	NPD7390	Discontinued
0.6074	Remote Similarity	NPD4574	Approved
0.6074	Remote Similarity	NPD4576	Approved
0.6071	Remote Similarity	NPD8368	Discontinued
0.6069	Remote Similarity	NPD6663	Approved
0.6065	Remote Similarity	NPD7606	Phase 3
0.6058	Remote Similarity	NPD1651	Approved
0.6056	Remote Similarity	NPD4980	Approved
0.6054	Remote Similarity	NPD6651	Approved
0.6053	Remote Similarity	NPD2309	Approved
0.6053	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD4380	Phase 2
0.6051	Remote Similarity	NPD6599	Discontinued
0.6049	Remote Similarity	NPD5494	Approved
0.6048	Remote Similarity	NPD4655	Approved
0.6048	Remote Similarity	NPD4657	Approved
0.6047	Remote Similarity	NPD6685	Approved
0.6045	Remote Similarity	NPD1711	Phase 2
0.6043	Remote Similarity	NPD7437	Approved
0.6043	Remote Similarity	NPD7436	Approved
0.6039	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD1752	Approved
0.6031	Remote Similarity	NPD1756	Approved
0.6026	Remote Similarity	NPD2800	Approved
0.6026	Remote Similarity	NPD7082	Approved
0.6024	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD9259	Approved
0.6017	Remote Similarity	NPD9257	Approved
0.6016	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD2607	Approved
0.6014	Remote Similarity	NPD4199	Phase 3
0.6014	Remote Similarity	NPD5736	Approved
0.6014	Remote Similarity	NPD17	Approved
0.6	Remote Similarity	NPD4198	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