NPASS Compound

Structure

NPC470820 OpenBabel07101719252D 28 30 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 -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 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 -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 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 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 0.0000 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 -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 17 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 18 2 0 0 0 0 8 18 1 0 0 0 0 9 12 2 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 19 2 0 0 0 0 11 20 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 22 1 0 0 0 0 14 19 1 0 0 0 0 14 25 1 0 0 0 0 15 21 1 0 0 0 0 15 26 1 0 0 0 0 16 1 1 6 0 0 0 16 17 1 0 0 0 0 17 20 1 0 0 0 0 19 21 1 0 0 0 0 20 24 1 6 0 0 0 21 24 1 6 0 0 0 22 24 1 6 0 0 0 22 28 1 0 0 0 0 23 27 2 0 0 0 0 23 28 1 0 0 0 0 24 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.21
Volume:	414.696
LogP:	3.691
LogD:	3.265
LogS:	-4.293
# Rotatable Bonds:	6
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.462
Synthetic Accessibility Score:	4.391
Fsp3:	0.458
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.474
MDCK Permeability:	2.8186323106638156e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.296
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.398
30% Bioavailability (F30%):	0.604

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.989
Plasma Protein Binding (PPB):	56.29924011230469%
Volume Distribution (VD):	0.95
Pgp-substrate:	46.272613525390625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.875
CYP1A2-substrate:	0.055
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.154
CYP2C9-substrate:	0.141
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.719
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	11.743
Half-life (T1/2):	0.23

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.227
Drug-inuced Liver Injury (DILI):	0.733
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.788
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.577
Carcinogencity:	0.614
Eye Corrosion:	0.689
Eye Irritation:	0.864
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC470820

Natural Product ID:	NPC470820
*Common Name:**	(1R,3S,4As,8S,8As)-7,8-Bis(Hydroxymethyl)-3,8A-Dimethyl-4-Methylene-1,2,3,4,4A,5,8,8A-Octahydronaphthalen-1-Yl Cinnamate
IUPAC Name:	[(1R,3S,4aS,8S,8aS)-7,8-bis(hydroxymethyl)-3,8a-dimethyl-4-methylidene-1,2,3,4a,5,8-hexahydronaphthalen-1-yl] (E)-3-phenylprop-2-enoate
Synonyms:
Standard InCHIKey:	VTIFJQDCHVYKFM-PKCWWXAYSA-N
Standard InCHI:	InChI=1S/C24H30O4/c1-16-13-22(28-23(27)12-9-18-7-5-4-6-8-18)24(3)20(17(16)2)11-10-19(14-25)21(24)15-26/h4-10,12,16,20-22,25-26H,2,11,13-15H2,1,3H3/b12-9+/t16-,20-,21-,22+,24-/m0/s1
SMILES:	CC1CC(C2(C(C1=C)CC=C(C2CO)CO)C)OC(=O)C=CC3=CC=CC=C3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2252778
PubChem CID:	11625136
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[485658]
NPT6576	Organism	Puccinia graminis f. tritici	Puccinia graminis f. tritici	Inhibition	=	0.0	%	PMID[485658]
NPT1095	Organism	Plasmopara viticola	Plasmopara viticola	Inhibition	=	4.0	%	PMID[485658]
NPT1095	Organism	Plasmopara viticola	Plasmopara viticola	Inhibition	=	22.0	%	PMID[485658]
NPT1095	Organism	Plasmopara viticola	Plasmopara viticola	Inhibition	=	70.0	%	PMID[485658]
NPT825	Organism	Phytophthora infestans	Phytophthora infestans	Inhibition	=	-6.0	%	PMID[485658]
NPT825	Organism	Phytophthora infestans	Phytophthora infestans	Inhibition	=	8.0	%	PMID[485658]
NPT825	Organism	Phytophthora infestans	Phytophthora infestans	Inhibition	=	58.0	%	PMID[485658]
NPT828	Organism	Phaeosphaeria nodorum	Phaeosphaeria nodorum	Inhibition	=	0.0	%	PMID[485658]

☑ 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 NPC470820 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	207
0.1-0.2	934
0.2-0.3	1882
0.3-0.4	4751
0.4-0.5	8542
0.5-0.6	17532
0.6-0.7	7891
0.7-0.8	864
0.8-0.85	69
0.85-0.9	22
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.931	High Similarity	NPC472373
0.931	High Similarity	NPC470815
0.9224	High Similarity	NPC12016
0.9153	High Similarity	NPC45821
0.9068	High Similarity	NPC471758
0.9	High Similarity	NPC230331
0.8974	High Similarity	NPC475328
0.8879	High Similarity	NPC470814
0.8824	High Similarity	NPC140118
0.8824	High Similarity	NPC12881
0.8793	High Similarity	NPC89324
0.877	High Similarity	NPC93632
0.8729	High Similarity	NPC473439
0.8729	High Similarity	NPC300827
0.8707	High Similarity	NPC84129
0.8699	High Similarity	NPC472388
0.8678	High Similarity	NPC475933
0.8678	High Similarity	NPC470816
0.8678	High Similarity	NPC470158
0.8655	High Similarity	NPC473749
0.8618	High Similarity	NPC225103
0.8607	High Similarity	NPC476972
0.8607	High Similarity	NPC476971
0.856	High Similarity	NPC80599
0.8548	High Similarity	NPC473443
0.8534	High Similarity	NPC476476
0.8525	High Similarity	NPC476970
0.8455	Intermediate Similarity	NPC5486
0.8448	Intermediate Similarity	NPC473869
0.8438	Intermediate Similarity	NPC472372
0.8438	Intermediate Similarity	NPC472374
0.843	Intermediate Similarity	NPC473870
0.843	Intermediate Similarity	NPC182333
0.843	Intermediate Similarity	NPC473871
0.843	Intermediate Similarity	NPC273336
0.8417	Intermediate Similarity	NPC311175
0.8417	Intermediate Similarity	NPC37641
0.8387	Intermediate Similarity	NPC58061
0.8374	Intermediate Similarity	NPC275576
0.8374	Intermediate Similarity	NPC470818
0.8361	Intermediate Similarity	NPC77691
0.8361	Intermediate Similarity	NPC307139
0.8347	Intermediate Similarity	NPC473889
0.8347	Intermediate Similarity	NPC70973
0.8306	Intermediate Similarity	NPC169913
0.8293	Intermediate Similarity	NPC474532
0.8293	Intermediate Similarity	NPC284022
0.8281	Intermediate Similarity	NPC48929
0.8268	Intermediate Similarity	NPC476976
0.8268	Intermediate Similarity	NPC209851
0.824	Intermediate Similarity	NPC195224
0.8235	Intermediate Similarity	NPC152812
0.8217	Intermediate Similarity	NPC477893
0.8211	Intermediate Similarity	NPC469742
0.8203	Intermediate Similarity	NPC15850
0.8189	Intermediate Similarity	NPC476977
0.8167	Intermediate Similarity	NPC473860
0.816	Intermediate Similarity	NPC190849
0.816	Intermediate Similarity	NPC253681
0.816	Intermediate Similarity	NPC171007
0.8145	Intermediate Similarity	NPC114927
0.8145	Intermediate Similarity	NPC473083
0.8145	Intermediate Similarity	NPC265413
0.8145	Intermediate Similarity	NPC10154
0.8106	Intermediate Similarity	NPC472547
0.8103	Intermediate Similarity	NPC133308
0.8092	Intermediate Similarity	NPC39549
0.808	Intermediate Similarity	NPC473110
0.808	Intermediate Similarity	NPC473082
0.808	Intermediate Similarity	NPC473111
0.8077	Intermediate Similarity	NPC477896
0.807	Intermediate Similarity	NPC477251
0.8047	Intermediate Similarity	NPC472418
0.8047	Intermediate Similarity	NPC72915
0.8034	Intermediate Similarity	NPC234376
0.8016	Intermediate Similarity	NPC473423
0.8015	Intermediate Similarity	NPC472545
0.8015	Intermediate Similarity	NPC472551
0.8	Intermediate Similarity	NPC204644
0.8	Intermediate Similarity	NPC38696
0.7985	Intermediate Similarity	NPC34012
0.7985	Intermediate Similarity	NPC473755
0.7985	Intermediate Similarity	NPC475513
0.797	Intermediate Similarity	NPC90614
0.797	Intermediate Similarity	NPC275592
0.797	Intermediate Similarity	NPC100913
0.7969	Intermediate Similarity	NPC86257
0.7969	Intermediate Similarity	NPC147561
0.7966	Intermediate Similarity	NPC265002
0.7939	Intermediate Similarity	NPC471864
0.7931	Intermediate Similarity	NPC64642
0.7931	Intermediate Similarity	NPC149455
0.7931	Intermediate Similarity	NPC472982
0.7926	Intermediate Similarity	NPC477894
0.791	Intermediate Similarity	NPC472576
0.791	Intermediate Similarity	NPC291599
0.791	Intermediate Similarity	NPC118080
0.791	Intermediate Similarity	NPC87448
0.791	Intermediate Similarity	NPC27377
0.791	Intermediate Similarity	NPC41481
0.791	Intermediate Similarity	NPC97947
0.7907	Intermediate Similarity	NPC472361
0.7903	Intermediate Similarity	NPC293831
0.7903	Intermediate Similarity	NPC369
0.7895	Intermediate Similarity	NPC472221
0.7895	Intermediate Similarity	NPC472222
0.7886	Intermediate Similarity	NPC133389
0.7886	Intermediate Similarity	NPC183339
0.7886	Intermediate Similarity	NPC234337
0.7874	Intermediate Similarity	NPC473220
0.7874	Intermediate Similarity	NPC470753
0.7869	Intermediate Similarity	NPC254233
0.7863	Intermediate Similarity	NPC126516
0.7863	Intermediate Similarity	NPC203486
0.7852	Intermediate Similarity	NPC140021
0.7851	Intermediate Similarity	NPC105141
0.7851	Intermediate Similarity	NPC242764
0.7846	Intermediate Similarity	NPC472394
0.7846	Intermediate Similarity	NPC475493
0.7845	Intermediate Similarity	NPC472980
0.7836	Intermediate Similarity	NPC116742
0.7836	Intermediate Similarity	NPC473440
0.7836	Intermediate Similarity	NPC139243
0.7836	Intermediate Similarity	NPC97667
0.7836	Intermediate Similarity	NPC171207
0.7829	Intermediate Similarity	NPC49272
0.7829	Intermediate Similarity	NPC475138
0.7826	Intermediate Similarity	NPC320734
0.782	Intermediate Similarity	NPC249817
0.782	Intermediate Similarity	NPC262324
0.782	Intermediate Similarity	NPC243893
0.781	Intermediate Similarity	NPC472556
0.7803	Intermediate Similarity	NPC473399
0.7803	Intermediate Similarity	NPC11266
0.7803	Intermediate Similarity	NPC473216
0.7803	Intermediate Similarity	NPC194970
0.7795	Intermediate Similarity	NPC470765
0.7794	Intermediate Similarity	NPC163087
0.7794	Intermediate Similarity	NPC20631
0.7794	Intermediate Similarity	NPC91703
0.7794	Intermediate Similarity	NPC93640
0.7786	Intermediate Similarity	NPC472437
0.7778	Intermediate Similarity	NPC224491
0.7778	Intermediate Similarity	NPC470616
0.7778	Intermediate Similarity	NPC16912
0.7778	Intermediate Similarity	NPC470617
0.7761	Intermediate Similarity	NPC198621
0.7761	Intermediate Similarity	NPC9905
0.7761	Intermediate Similarity	NPC22676
0.7761	Intermediate Similarity	NPC216940
0.7761	Intermediate Similarity	NPC475482
0.7759	Intermediate Similarity	NPC136962
0.7759	Intermediate Similarity	NPC37115
0.7744	Intermediate Similarity	NPC477874
0.7744	Intermediate Similarity	NPC173569
0.7737	Intermediate Similarity	NPC111466
0.7737	Intermediate Similarity	NPC470152
0.7737	Intermediate Similarity	NPC241951
0.7737	Intermediate Similarity	NPC475759
0.7737	Intermediate Similarity	NPC475122
0.7727	Intermediate Similarity	NPC474608
0.7727	Intermediate Similarity	NPC310662
0.7727	Intermediate Similarity	NPC329913
0.7721	Intermediate Similarity	NPC472546
0.7721	Intermediate Similarity	NPC63737
0.7721	Intermediate Similarity	NPC172311
0.7721	Intermediate Similarity	NPC192658
0.771	Intermediate Similarity	NPC471880
0.7704	Intermediate Similarity	NPC87934
0.7704	Intermediate Similarity	NPC162613
0.7704	Intermediate Similarity	NPC182249
0.7704	Intermediate Similarity	NPC79921
0.7698	Intermediate Similarity	NPC478058
0.7698	Intermediate Similarity	NPC217918
0.7692	Intermediate Similarity	NPC131684
0.7692	Intermediate Similarity	NPC27252
0.7692	Intermediate Similarity	NPC288290
0.7692	Intermediate Similarity	NPC472979
0.7692	Intermediate Similarity	NPC21929
0.7681	Intermediate Similarity	NPC184817
0.7681	Intermediate Similarity	NPC174982
0.7681	Intermediate Similarity	NPC158663
0.7681	Intermediate Similarity	NPC40085
0.7681	Intermediate Similarity	NPC301946
0.7681	Intermediate Similarity	NPC472572
0.7681	Intermediate Similarity	NPC469349
0.7681	Intermediate Similarity	NPC472571
0.7681	Intermediate Similarity	NPC171525
0.7681	Intermediate Similarity	NPC476973
0.7681	Intermediate Similarity	NPC200471
0.7681	Intermediate Similarity	NPC177940
0.7681	Intermediate Similarity	NPC472568
0.7681	Intermediate Similarity	NPC473088
0.7681	Intermediate Similarity	NPC264270
0.7681	Intermediate Similarity	NPC277053
0.7681	Intermediate Similarity	NPC470159
0.7681	Intermediate Similarity	NPC70403
0.7681	Intermediate Similarity	NPC472575
0.7681	Intermediate Similarity	NPC96903
0.7681	Intermediate Similarity	NPC470157

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 NPC470820 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	714
0.2-0.3	1301
0.3-0.4	2828
0.4-0.5	2243
0.5-0.6	1529
0.6-0.7	331
0.7-0.8	20
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
0.7724	Intermediate Similarity	NPD7741	Discontinued
0.7652	Intermediate Similarity	NPD6647	Phase 2
0.7541	Intermediate Similarity	NPD2629	Approved
0.7482	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD4198	Discontinued
0.746	Intermediate Similarity	NPD5125	Phase 3
0.746	Intermediate Similarity	NPD5126	Approved
0.7459	Intermediate Similarity	NPD6010	Discontinued
0.7436	Intermediate Similarity	NPD5909	Discontinued
0.7429	Intermediate Similarity	NPD7236	Approved
0.7424	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD6858	Approved
0.7377	Intermediate Similarity	NPD7094	Approved
0.7373	Intermediate Similarity	NPD5048	Discontinued
0.7328	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6685	Approved
0.7293	Intermediate Similarity	NPD7008	Discontinued
0.7258	Intermediate Similarity	NPD5951	Approved
0.7193	Intermediate Similarity	NPD6049	Phase 2
0.7193	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7239	Suspended
0.7163	Intermediate Similarity	NPD8166	Discontinued
0.7143	Intermediate Similarity	NPD5736	Approved
0.7132	Intermediate Similarity	NPD4140	Approved
0.7105	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD2066	Phase 3
0.7073	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5765	Approved
0.7059	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4628	Phase 3
0.704	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5926	Approved
0.7007	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3971	Phase 1
0.695	Remote Similarity	NPD5763	Approved
0.695	Remote Similarity	NPD5762	Approved
0.695	Remote Similarity	NPD7266	Discontinued
0.6949	Remote Similarity	NPD7640	Approved
0.6949	Remote Similarity	NPD7639	Approved
0.694	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD7961	Discontinued
0.6934	Remote Similarity	NPD6663	Approved
0.6923	Remote Similarity	NPD4626	Approved
0.6923	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1930	Approved
0.6917	Remote Similarity	NPD1929	Approved
0.6911	Remote Similarity	NPD2182	Approved
0.6899	Remote Similarity	NPD3091	Approved
0.688	Remote Similarity	NPD6912	Phase 3
0.6875	Remote Similarity	NPD1282	Approved
0.687	Remote Similarity	NPD3496	Discontinued
0.6866	Remote Similarity	NPD3094	Phase 2
0.6864	Remote Similarity	NPD7638	Approved
0.6861	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2067	Discontinued
0.6849	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD5691	Approved
0.6842	Remote Similarity	NPD7057	Phase 3
0.6842	Remote Similarity	NPD7058	Phase 2
0.6835	Remote Similarity	NPD5124	Phase 1
0.6835	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3092	Approved
0.6809	Remote Similarity	NPD7305	Phase 1
0.6803	Remote Similarity	NPD6273	Approved
0.6794	Remote Similarity	NPD3095	Discontinued
0.6779	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8127	Discontinued
0.6772	Remote Similarity	NPD7799	Discontinued
0.6767	Remote Similarity	NPD6637	Approved
0.6763	Remote Similarity	NPD4060	Phase 1
0.6754	Remote Similarity	NPD689	Discontinued
0.6739	Remote Similarity	NPD3764	Approved
0.673	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD1088	Approved
0.6713	Remote Similarity	NPD6002	Phase 3
0.6713	Remote Similarity	NPD6005	Phase 3
0.6713	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6004	Phase 3
0.6695	Remote Similarity	NPD1989	Approved
0.6692	Remote Similarity	NPD6287	Discontinued
0.669	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2932	Approved
0.6642	Remote Similarity	NPD2861	Phase 2
0.6621	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD2797	Approved
0.6615	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD5706	Approved
0.6613	Remote Similarity	NPD5704	Approved
0.6613	Remote Similarity	NPD5705	Approved
0.6605	Remote Similarity	NPD8368	Discontinued
0.6597	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD2346	Discontinued
0.6596	Remote Similarity	NPD5735	Approved
0.6591	Remote Similarity	NPD7503	Approved
0.6591	Remote Similarity	NPD5585	Approved
0.6585	Remote Similarity	NPD1237	Approved
0.6585	Remote Similarity	NPD164	Approved
0.6583	Remote Similarity	NPD4225	Approved
0.6573	Remote Similarity	NPD7033	Discontinued
0.6571	Remote Similarity	NPD7714	Approved
0.6571	Remote Similarity	NPD7715	Approved
0.6569	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6085	Phase 2
0.6565	Remote Similarity	NPD7610	Discontinued
0.6562	Remote Similarity	NPD7635	Approved
0.6557	Remote Similarity	NPD1932	Approved
0.6556	Remote Similarity	NPD3226	Approved
0.6552	Remote Similarity	NPD1086	Approved
0.6552	Remote Similarity	NPD1089	Approved
0.6552	Remote Similarity	NPD1090	Approved
0.6552	Remote Similarity	NPD3672	Approved
0.6552	Remote Similarity	NPD3673	Approved
0.6544	Remote Similarity	NPD8651	Approved
0.6541	Remote Similarity	NPD3019	Approved
0.6538	Remote Similarity	NPD3317	Approved
0.6536	Remote Similarity	NPD37	Approved
0.6531	Remote Similarity	NPD6190	Approved
0.6529	Remote Similarity	NPD7798	Approved
0.6529	Remote Similarity	NPD1238	Approved
0.6529	Remote Similarity	NPD6648	Approved
0.6519	Remote Similarity	NPD1608	Approved
0.6516	Remote Similarity	NPD4967	Phase 2
0.6516	Remote Similarity	NPD4966	Approved
0.6516	Remote Similarity	NPD4965	Approved
0.6515	Remote Similarity	NPD7009	Phase 2
0.6515	Remote Similarity	NPD9545	Approved
0.6508	Remote Similarity	NPD2329	Discontinued
0.6507	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD8434	Phase 2
0.6503	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3268	Approved
0.65	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3495	Discontinued
0.6485	Remote Similarity	NPD8407	Phase 2
0.6484	Remote Similarity	NPD969	Suspended
0.648	Remote Similarity	NPD3134	Approved
0.6475	Remote Similarity	NPD5344	Discontinued
0.6475	Remote Similarity	NPD4908	Phase 1
0.6475	Remote Similarity	NPD7055	Discontinued
0.6471	Remote Similarity	NPD1693	Approved
0.6471	Remote Similarity	NPD4749	Approved
0.6471	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5327	Phase 3
0.6467	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD800	Approved
0.6463	Remote Similarity	NPD3750	Approved
0.6462	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5239	Approved
0.6457	Remote Similarity	NPD5235	Approved
0.6457	Remote Similarity	NPD5236	Approved
0.6457	Remote Similarity	NPD5240	Approved
0.6457	Remote Similarity	NPD4750	Phase 3
0.6457	Remote Similarity	NPD5237	Approved
0.6447	Remote Similarity	NPD7458	Discontinued
0.6446	Remote Similarity	NPD9495	Approved
0.6444	Remote Similarity	NPD1611	Approved
0.6434	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8360	Approved
0.6429	Remote Similarity	NPD7095	Approved
0.6429	Remote Similarity	NPD4625	Phase 3
0.6429	Remote Similarity	NPD8361	Approved
0.6423	Remote Similarity	NPD6696	Suspended
0.6423	Remote Similarity	NPD7632	Discontinued
0.6423	Remote Similarity	NPD1283	Approved
0.642	Remote Similarity	NPD5844	Phase 1
0.6418	Remote Similarity	NPD5305	Approved
0.6418	Remote Similarity	NPD5306	Approved
0.6418	Remote Similarity	NPD7725	Approved
0.6414	Remote Similarity	NPD6099	Approved
0.6414	Remote Similarity	NPD6100	Approved
0.6414	Remote Similarity	NPD2935	Discontinued
0.6414	Remote Similarity	NPD5405	Approved
0.6414	Remote Similarity	NPD5408	Approved
0.6414	Remote Similarity	NPD5406	Approved
0.6414	Remote Similarity	NPD5404	Approved
0.6408	Remote Similarity	NPD3620	Phase 2
0.6408	Remote Similarity	NPD2979	Phase 3
0.6408	Remote Similarity	NPD2238	Phase 2
0.6408	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD3020	Approved
0.6389	Remote Similarity	NPD5886	Approved
0.6389	Remote Similarity	NPD9716	Approved
0.6389	Remote Similarity	NPD7097	Phase 1
0.6389	Remote Similarity	NPD41	Approved
0.6387	Remote Similarity	NPD7819	Suspended
0.6383	Remote Similarity	NPD2313	Discontinued
0.6377	Remote Similarity	NPD1470	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