NPASS Compound

Structure

NPC12881 OpenBabel07101718232D 29 31 0 0 1 0 0 0 0 0999 V2000 0.0000 3.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 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 -4.3301 -2.5000 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 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 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 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 -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 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 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 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 16 2 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 17 2 0 0 0 0 8 17 1 0 0 0 0 9 10 2 0 0 0 0 9 17 1 0 0 0 0 10 22 1 0 0 0 0 11 15 1 0 0 0 0 11 21 1 0 0 0 0 12 18 2 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 13 25 2 0 0 0 0 14 19 1 0 0 0 0 14 26 2 0 0 0 0 15 1 1 6 0 0 0 15 16 1 0 0 0 0 16 23 1 0 0 0 0 18 19 1 0 0 0 0 19 24 1 6 0 0 0 20 23 1 0 0 0 0 20 27 1 1 0 0 0 21 24 1 6 0 0 0 21 29 1 0 0 0 0 22 28 2 0 0 0 0 22 29 1 0 0 0 0 23 24 1 6 0 0 0 24 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.18
Volume:	418.214
LogP:	2.33
LogD:	1.718
LogS:	-4.103
# Rotatable Bonds:	6
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.359
Synthetic Accessibility Score:	4.66
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.851
MDCK Permeability:	1.645003976591397e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.476
Human Intestinal Absorption (HIA):	0.24
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.06

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.956
Plasma Protein Binding (PPB):	59.409217834472656%
Volume Distribution (VD):	1.922
Pgp-substrate:	43.98670196533203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.682
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.148
CYP2C9-substrate:	0.127
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.563
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	7.094
Half-life (T1/2):	0.38

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.923
Drug-inuced Liver Injury (DILI):	0.401
AMES Toxicity:	0.078
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.95
Carcinogencity:	0.375
Eye Corrosion:	0.979
Eye Irritation:	0.959
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC12881

Natural Product ID:	NPC12881
*Common Name:**	(1R,3S,4As,5S,8R,8As)-7,8-Diformyl-5-Hydroxy-3,8A-Dimethyl-4-Methylene-1,2,3,4,4A,5,8,8A-Octahydronaphthalen-1-Yl Cinnamate
IUPAC Name:	[(1R,3S,4aS,5S,8R,8aS)-7,8-diformyl-5-hydroxy-3,8a-dimethyl-4-methylidene-1,2,3,4a,5,8-hexahydronaphthalen-1-yl] (E)-3-phenylprop-2-enoate
Synonyms:
Standard InCHIKey:	OKDTYBVVAITUOQ-HNESARCWSA-N
Standard InCHI:	InChI=1S/C24H26O5/c1-15-11-21(29-22(28)10-9-17-7-5-4-6-8-17)24(3)19(14-26)18(13-25)12-20(27)23(24)16(15)2/h4-10,12-15,19-21,23,27H,2,11H2,1,3H3/b10-9+/t15-,19-,20-,21+,23+,24-/m0/s1
SMILES:	O=C[C@H]1C(=C[C@@H]([C@@H]2[C@]1(C)[C@H](OC(=O)/C=C/c1ccccc1)C[C@@H](C2=C)C)O)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2252769
PubChem CID:	11682657
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO12007	Pseudowintera axillaris	Species	Winteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16417306]
NPO12007	Pseudowintera axillaris	Species	Winteraceae	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	15

Activity Type	# Activity
Organism	15

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT827	Organism	Mycosphaerella graminicola	Mycosphaerella graminicola	Inhibition	=	0.0	%	PMID[505561]
NPT6576	Organism	Puccinia graminis f. tritici	Puccinia graminis f. tritici	Inhibition	=	4.0	%	PMID[505561]
NPT6576	Organism	Puccinia graminis f. tritici	Puccinia graminis f. tritici	Inhibition	=	15.0	%	PMID[505561]
NPT6576	Organism	Puccinia graminis f. tritici	Puccinia graminis f. tritici	Inhibition	=	85.0	%	PMID[505561]
NPT1095	Organism	Plasmopara viticola	Plasmopara viticola	Inhibition	=	2.0	%	PMID[505561]
NPT1095	Organism	Plasmopara viticola	Plasmopara viticola	Inhibition	=	19.0	%	PMID[505561]
NPT1095	Organism	Plasmopara viticola	Plasmopara viticola	Inhibition	=	89.0	%	PMID[505561]
NPT825	Organism	Phytophthora infestans	Phytophthora infestans	Inhibition	=	74.0	%	PMID[505561]
NPT825	Organism	Phytophthora infestans	Phytophthora infestans	Inhibition	=	91.0	%	PMID[505561]
NPT825	Organism	Phytophthora infestans	Phytophthora infestans	Inhibition	=	100.0	%	PMID[505561]
NPT828	Organism	Phaeosphaeria nodorum	Phaeosphaeria nodorum	Inhibition	=	33.0	%	PMID[505561]
NPT828	Organism	Phaeosphaeria nodorum	Phaeosphaeria nodorum	Inhibition	=	73.0	%	PMID[505561]
NPT828	Organism	Phaeosphaeria nodorum	Phaeosphaeria nodorum	Inhibition	=	96.0	%	PMID[505561]

☑ 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 NPC12881 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	232
0.1-0.2	923
0.2-0.3	1924
0.3-0.4	4786
0.4-0.5	8587
0.5-0.6	16640
0.6-0.7	8435
0.7-0.8	1119
0.8-0.85	43
0.85-0.9	4
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC140118
0.9397	High Similarity	NPC152812
0.8837	High Similarity	NPC194970
0.8824	High Similarity	NPC470820
0.8651	High Similarity	NPC169913
0.8594	High Similarity	NPC472388
0.8571	High Similarity	NPC275576
0.8516	High Similarity	NPC225103
0.8462	Intermediate Similarity	NPC80599
0.845	Intermediate Similarity	NPC473443
0.8425	Intermediate Similarity	NPC470816
0.8425	Intermediate Similarity	NPC470818
0.8409	Intermediate Similarity	NPC477893
0.8409	Intermediate Similarity	NPC477896
0.8359	Intermediate Similarity	NPC171007
0.8359	Intermediate Similarity	NPC190849
0.8333	Intermediate Similarity	NPC329913
0.8333	Intermediate Similarity	NPC126516
0.8295	Intermediate Similarity	NPC51448
0.8295	Intermediate Similarity	NPC115797
0.8268	Intermediate Similarity	NPC472373
0.8268	Intermediate Similarity	NPC470815
0.8258	Intermediate Similarity	NPC15850
0.8217	Intermediate Similarity	NPC473423
0.8217	Intermediate Similarity	NPC253681
0.8209	Intermediate Similarity	NPC472374
0.8209	Intermediate Similarity	NPC472372
0.8195	Intermediate Similarity	NPC203486
0.8189	Intermediate Similarity	NPC12016
0.8182	Intermediate Similarity	NPC209851
0.816	Intermediate Similarity	NPC204784
0.816	Intermediate Similarity	NPC202015
0.8154	Intermediate Similarity	NPC195224
0.814	Intermediate Similarity	NPC45821
0.8125	Intermediate Similarity	NPC469742
0.8116	Intermediate Similarity	NPC477894
0.8116	Intermediate Similarity	NPC477468
0.811	Intermediate Similarity	NPC293831
0.811	Intermediate Similarity	NPC369
0.8095	Intermediate Similarity	NPC234337
0.8095	Intermediate Similarity	NPC183339
0.8095	Intermediate Similarity	NPC133389
0.8077	Intermediate Similarity	NPC473220
0.8077	Intermediate Similarity	NPC470753
0.8077	Intermediate Similarity	NPC5486
0.8062	Intermediate Similarity	NPC295664
0.8062	Intermediate Similarity	NPC471758
0.806	Intermediate Similarity	NPC48929
0.8047	Intermediate Similarity	NPC182333
0.8047	Intermediate Similarity	NPC273336
0.803	Intermediate Similarity	NPC475138
0.8029	Intermediate Similarity	NPC473440
0.8015	Intermediate Similarity	NPC249817
0.8015	Intermediate Similarity	NPC230331
0.8	Intermediate Similarity	NPC470765
0.7984	Intermediate Similarity	NPC77691
0.7984	Intermediate Similarity	NPC307139
0.7984	Intermediate Similarity	NPC328107
0.797	Intermediate Similarity	NPC472418
0.7969	Intermediate Similarity	NPC475328
0.7956	Intermediate Similarity	NPC216940
0.7956	Intermediate Similarity	NPC475482
0.7956	Intermediate Similarity	NPC22676
0.7956	Intermediate Similarity	NPC198621
0.7953	Intermediate Similarity	NPC475827
0.7953	Intermediate Similarity	NPC474223
0.7941	Intermediate Similarity	NPC477874
0.7941	Intermediate Similarity	NPC173569
0.7939	Intermediate Similarity	NPC477365
0.7937	Intermediate Similarity	NPC254233
0.7926	Intermediate Similarity	NPC310662
0.792	Intermediate Similarity	NPC105141
0.792	Intermediate Similarity	NPC242764
0.7914	Intermediate Similarity	NPC172311
0.7914	Intermediate Similarity	NPC63737
0.7914	Intermediate Similarity	NPC140021
0.7899	Intermediate Similarity	NPC472547
0.7899	Intermediate Similarity	NPC79921
0.7895	Intermediate Similarity	NPC49272
0.7895	Intermediate Similarity	NPC131684
0.7891	Intermediate Similarity	NPC472981
0.7886	Intermediate Similarity	NPC128368
0.7886	Intermediate Similarity	NPC287055
0.7886	Intermediate Similarity	NPC242957
0.7886	Intermediate Similarity	NPC206414
0.7886	Intermediate Similarity	NPC306977
0.7883	Intermediate Similarity	NPC39549
0.7879	Intermediate Similarity	NPC477370
0.7874	Intermediate Similarity	NPC470814
0.7872	Intermediate Similarity	NPC25491
0.7872	Intermediate Similarity	NPC301946
0.7872	Intermediate Similarity	NPC277053
0.7868	Intermediate Similarity	NPC471864
0.7863	Intermediate Similarity	NPC477366
0.7863	Intermediate Similarity	NPC137416
0.7857	Intermediate Similarity	NPC45794
0.7847	Intermediate Similarity	NPC197037
0.7846	Intermediate Similarity	NPC85511
0.7836	Intermediate Similarity	NPC472361
0.7836	Intermediate Similarity	NPC72915
0.7823	Intermediate Similarity	NPC153053
0.782	Intermediate Similarity	NPC93632
0.7812	Intermediate Similarity	NPC475804
0.7812	Intermediate Similarity	NPC474222
0.781	Intermediate Similarity	NPC472551
0.781	Intermediate Similarity	NPC472545
0.7801	Intermediate Similarity	NPC38696
0.7801	Intermediate Similarity	NPC80895
0.7801	Intermediate Similarity	NPC471912
0.7795	Intermediate Similarity	NPC89324
0.7794	Intermediate Similarity	NPC4242
0.7794	Intermediate Similarity	NPC471911
0.7786	Intermediate Similarity	NPC474532
0.7786	Intermediate Similarity	NPC472801
0.7786	Intermediate Similarity	NPC182869
0.7786	Intermediate Similarity	NPC34012
0.7786	Intermediate Similarity	NPC304110
0.7786	Intermediate Similarity	NPC27518
0.7778	Intermediate Similarity	NPC165260
0.7778	Intermediate Similarity	NPC475493
0.7778	Intermediate Similarity	NPC91730
0.7778	Intermediate Similarity	NPC198455
0.7778	Intermediate Similarity	NPC472394
0.7778	Intermediate Similarity	NPC212891
0.7778	Intermediate Similarity	NPC161239
0.777	Intermediate Similarity	NPC275592
0.777	Intermediate Similarity	NPC100913
0.777	Intermediate Similarity	NPC90614
0.7769	Intermediate Similarity	NPC474159
0.7769	Intermediate Similarity	NPC474254
0.7769	Intermediate Similarity	NPC20485
0.7769	Intermediate Similarity	NPC21929
0.7761	Intermediate Similarity	NPC471832
0.7761	Intermediate Similarity	NPC262819
0.7761	Intermediate Similarity	NPC147561
0.776	Intermediate Similarity	NPC221275
0.7754	Intermediate Similarity	NPC262324
0.7754	Intermediate Similarity	NPC184109
0.7754	Intermediate Similarity	NPC243893
0.7752	Intermediate Similarity	NPC473439
0.7752	Intermediate Similarity	NPC300827
0.7746	Intermediate Similarity	NPC127857
0.774	Intermediate Similarity	NPC248265
0.774	Intermediate Similarity	NPC229545
0.774	Intermediate Similarity	NPC11588
0.774	Intermediate Similarity	NPC134685
0.7737	Intermediate Similarity	NPC23894
0.7734	Intermediate Similarity	NPC476645
0.773	Intermediate Similarity	NPC95449
0.7727	Intermediate Similarity	NPC477363
0.7727	Intermediate Similarity	NPC470158
0.7727	Intermediate Similarity	NPC475933
0.7727	Intermediate Similarity	NPC473082
0.7724	Intermediate Similarity	NPC473719
0.7721	Intermediate Similarity	NPC472656
0.7721	Intermediate Similarity	NPC472437
0.7717	Intermediate Similarity	NPC222968
0.7717	Intermediate Similarity	NPC80605
0.7717	Intermediate Similarity	NPC323440
0.7717	Intermediate Similarity	NPC84129
0.7714	Intermediate Similarity	NPC472576
0.7714	Intermediate Similarity	NPC41481
0.7714	Intermediate Similarity	NPC291599
0.7714	Intermediate Similarity	NPC27377
0.7714	Intermediate Similarity	NPC118080
0.7714	Intermediate Similarity	NPC87448
0.7714	Intermediate Similarity	NPC97947
0.771	Intermediate Similarity	NPC472681
0.771	Intermediate Similarity	NPC318067
0.771	Intermediate Similarity	NPC477362
0.7708	Intermediate Similarity	NPC250046
0.7708	Intermediate Similarity	NPC60509
0.7708	Intermediate Similarity	NPC81698
0.7704	Intermediate Similarity	NPC470278
0.7692	Intermediate Similarity	NPC167323
0.7692	Intermediate Similarity	NPC473749
0.7692	Intermediate Similarity	NPC329387
0.7692	Intermediate Similarity	NPC269923
0.7692	Intermediate Similarity	NPC317280
0.7687	Intermediate Similarity	NPC37968
0.7687	Intermediate Similarity	NPC114357
0.7687	Intermediate Similarity	NPC155329
0.7687	Intermediate Similarity	NPC259144
0.7686	Intermediate Similarity	NPC142326
0.7686	Intermediate Similarity	NPC94751
0.7686	Intermediate Similarity	NPC477251
0.7676	Intermediate Similarity	NPC111466
0.7674	Intermediate Similarity	NPC473243
0.7674	Intermediate Similarity	NPC470585
0.7671	Intermediate Similarity	NPC87630
0.7671	Intermediate Similarity	NPC179128
0.7671	Intermediate Similarity	NPC472548
0.7671	Intermediate Similarity	NPC267469
0.7671	Intermediate Similarity	NPC116292
0.7669	Intermediate Similarity	NPC477357
0.7669	Intermediate Similarity	NPC476972
0.7669	Intermediate Similarity	NPC476971
0.7669	Intermediate Similarity	NPC51292
0.7664	Intermediate Similarity	NPC475627
0.7664	Intermediate Similarity	NPC475457

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 NPC12881 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	713
0.2-0.3	1347
0.3-0.4	2765
0.4-0.5	2302
0.5-0.6	1394
0.6-0.7	399
0.7-0.8	24
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
0.7872	Intermediate Similarity	NPD7236	Approved
0.7823	Intermediate Similarity	NPD6010	Discontinued
0.776	Intermediate Similarity	NPD2629	Approved
0.7667	Intermediate Similarity	NPD5909	Discontinued
0.763	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD7239	Suspended
0.76	Intermediate Similarity	NPD6858	Approved
0.76	Intermediate Similarity	NPD7094	Approved
0.7583	Intermediate Similarity	NPD6647	Phase 2
0.75	Intermediate Similarity	NPD7008	Discontinued
0.748	Intermediate Similarity	NPD5951	Approved
0.7419	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2182	Approved
0.7405	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7961	Discontinued
0.7376	Intermediate Similarity	NPD7305	Phase 1
0.7361	Intermediate Similarity	NPD8166	Discontinued
0.735	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2066	Phase 3
0.7317	Intermediate Similarity	NPD5048	Discontinued
0.7302	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7058	Phase 2
0.7255	Intermediate Similarity	NPD7057	Phase 3
0.7222	Intermediate Similarity	NPD2067	Discontinued
0.7218	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1930	Approved
0.7154	Intermediate Similarity	NPD3317	Approved
0.7154	Intermediate Similarity	NPD1929	Approved
0.7154	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD4198	Discontinued
0.7153	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6663	Approved
0.7123	Intermediate Similarity	NPD4628	Phase 3
0.7101	Intermediate Similarity	NPD5736	Approved
0.7097	Intermediate Similarity	NPD164	Approved
0.7073	Intermediate Similarity	NPD1932	Approved
0.7034	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD2329	Discontinued
0.7	Intermediate Similarity	NPD6273	Approved
0.6988	Remote Similarity	NPD8434	Phase 2
0.6984	Remote Similarity	NPD6685	Approved
0.6977	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1088	Approved
0.6942	Remote Similarity	NPD1989	Approved
0.6933	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2346	Discontinued
0.6912	Remote Similarity	NPD6287	Discontinued
0.6906	Remote Similarity	NPD6085	Phase 2
0.6906	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD7003	Approved
0.6892	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2932	Approved
0.6866	Remote Similarity	NPD7741	Discontinued
0.6863	Remote Similarity	NPD7458	Discontinued
0.6863	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6637	Approved
0.6852	Remote Similarity	NPD7799	Discontinued
0.6835	Remote Similarity	NPD2797	Approved
0.6831	Remote Similarity	NPD3268	Approved
0.6825	Remote Similarity	NPD1237	Approved
0.6807	Remote Similarity	NPD3673	Approved
0.6807	Remote Similarity	NPD1090	Approved
0.6807	Remote Similarity	NPD3672	Approved
0.6807	Remote Similarity	NPD1089	Approved
0.6807	Remote Similarity	NPD1086	Approved
0.6803	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7610	Discontinued
0.6788	Remote Similarity	NPD8368	Discontinued
0.6783	Remote Similarity	NPD7714	Approved
0.6783	Remote Similarity	NPD7715	Approved
0.6774	Remote Similarity	NPD7798	Approved
0.6774	Remote Similarity	NPD1238	Approved
0.6765	Remote Similarity	NPD3019	Approved
0.6753	Remote Similarity	NPD3226	Approved
0.6753	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.675	Remote Similarity	NPD8127	Discontinued
0.6748	Remote Similarity	NPD3495	Discontinued
0.6746	Remote Similarity	NPD5765	Approved
0.6741	Remote Similarity	NPD7009	Phase 2
0.6736	Remote Similarity	NPD4140	Approved
0.6733	Remote Similarity	NPD6190	Approved
0.6733	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD800	Approved
0.6721	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6049	Phase 2
0.6721	Remote Similarity	NPD1693	Approved
0.6713	Remote Similarity	NPD3764	Approved
0.6713	Remote Similarity	NPD2313	Discontinued
0.6711	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD9495	Approved
0.6694	Remote Similarity	NPD5926	Approved
0.6692	Remote Similarity	NPD1317	Discontinued
0.6692	Remote Similarity	NPD690	Clinical (unspecified phase)
0.669	Remote Similarity	NPD7055	Discontinued
0.6688	Remote Similarity	NPD5760	Phase 2
0.6688	Remote Similarity	NPD5761	Phase 2
0.6687	Remote Similarity	NPD6764	Approved
0.6687	Remote Similarity	NPD6765	Approved
0.6667	Remote Similarity	NPD6065	Approved
0.6667	Remote Similarity	NPD8407	Phase 2
0.6667	Remote Similarity	NPD2799	Discontinued
0.6644	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1283	Approved
0.6642	Remote Similarity	NPD5306	Approved
0.6642	Remote Similarity	NPD5125	Phase 3
0.6642	Remote Similarity	NPD5126	Approved
0.6642	Remote Similarity	NPD5305	Approved
0.6642	Remote Similarity	NPD7115	Discovery
0.6641	Remote Similarity	NPD6649	Approved
0.6641	Remote Similarity	NPD6650	Approved
0.6622	Remote Similarity	NPD2935	Discontinued
0.6621	Remote Similarity	NPD2979	Phase 3
0.6619	Remote Similarity	NPD1608	Approved
0.6619	Remote Similarity	NPD4878	Approved
0.6618	Remote Similarity	NPD9545	Approved
0.6617	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD1565	Approved
0.6613	Remote Similarity	NPD1566	Phase 3
0.6613	Remote Similarity	NPD1564	Approved
0.6613	Remote Similarity	NPD7902	Approved
0.6612	Remote Similarity	NPD1239	Approved
0.6608	Remote Similarity	NPD8361	Approved
0.6608	Remote Similarity	NPD8360	Approved
0.6606	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1470	Approved
0.6591	Remote Similarity	NPD6912	Phase 3
0.6589	Remote Similarity	NPD5697	Approved
0.6588	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD5346	Phase 2
0.6583	Remote Similarity	NPD5347	Phase 2
0.6577	Remote Similarity	NPD6002	Phase 3
0.6577	Remote Similarity	NPD6004	Phase 3
0.6577	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6005	Phase 3
0.6575	Remote Similarity	NPD6355	Discontinued
0.6569	Remote Similarity	NPD5981	Approved
0.6569	Remote Similarity	NPD5585	Approved
0.656	Remote Similarity	NPD4225	Approved
0.6557	Remote Similarity	NPD7631	Approved
0.6556	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4110	Phase 3
0.6555	Remote Similarity	NPD1087	Approved
0.6554	Remote Similarity	NPD7033	Discontinued
0.6552	Remote Similarity	NPD8032	Phase 2
0.6547	Remote Similarity	NPD4806	Approved
0.6547	Remote Similarity	NPD4807	Approved
0.6538	Remote Similarity	NPD6899	Approved
0.6538	Remote Similarity	NPD6881	Approved
0.6538	Remote Similarity	NPD6011	Approved
0.6532	Remote Similarity	NPD4697	Phase 3
0.6529	Remote Similarity	NPD6784	Approved
0.6529	Remote Similarity	NPD6785	Approved
0.6525	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4626	Approved
0.6522	Remote Similarity	NPD1778	Approved
0.6519	Remote Similarity	NPD37	Approved
0.6512	Remote Similarity	NPD8435	Approved
0.651	Remote Similarity	NPD6099	Approved
0.651	Remote Similarity	NPD6100	Approved
0.6508	Remote Similarity	NPD7640	Approved
0.6508	Remote Similarity	NPD7639	Approved
0.6506	Remote Similarity	NPD5844	Phase 1
0.65	Remote Similarity	NPD3972	Approved
0.65	Remote Similarity	NPD4965	Approved
0.65	Remote Similarity	NPD4967	Phase 2
0.65	Remote Similarity	NPD4966	Approved
0.6496	Remote Similarity	NPD3971	Phase 1
0.6496	Remote Similarity	NPD3091	Approved
0.6494	Remote Similarity	NPD2532	Approved
0.6494	Remote Similarity	NPD2534	Approved
0.6494	Remote Similarity	NPD2533	Approved
0.6491	Remote Similarity	NPD8150	Discontinued
0.6489	Remote Similarity	NPD6014	Approved
0.6489	Remote Similarity	NPD6373	Approved
0.6489	Remote Similarity	NPD6013	Approved
0.6489	Remote Similarity	NPD6372	Approved
0.6489	Remote Similarity	NPD6012	Approved
0.6486	Remote Similarity	NPD7097	Phase 1
0.6483	Remote Similarity	NPD6798	Discontinued
0.6479	Remote Similarity	NPD3266	Approved
0.6479	Remote Similarity	NPD3267	Approved
0.6478	Remote Similarity	NPD7819	Suspended
0.6475	Remote Similarity	NPD3496	Discontinued
0.6475	Remote Similarity	NPD4135	Approved
0.6475	Remote Similarity	NPD7609	Phase 3
0.6475	Remote Similarity	NPD4106	Approved
0.6475	Remote Similarity	NPD3026	Approved
0.6475	Remote Similarity	NPD4879	Approved
0.6475	Remote Similarity	NPD6411	Approved
0.6475	Remote Similarity	NPD4136	Approved
0.6475	Remote Similarity	NPD3023	Approved
0.6466	Remote Similarity	NPD226	Approved
0.6449	Remote Similarity	NPD3025	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