NPASS Compound

Structure

NPC270811 OpenBabel07101718322D 27 29 0 0 1 0 0 0 0 0999 V2000 0.9889 4.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8549 5.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4530 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9889 3.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7210 4.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5870 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3190 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1229 3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5870 5.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5870 3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3190 3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 3.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4530 4.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 3.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4530 3.6691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 4.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3190 5.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 3.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -0.8090 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 1 4 1 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 17 1 0 0 0 0 9 20 1 0 0 0 0 10 11 2 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 12 22 1 0 0 0 0 13 22 1 0 0 0 0 14 16 2 0 0 0 0 14 19 1 0 0 0 0 15 26 1 0 0 0 0 15 27 1 0 0 0 0 16 21 1 0 0 0 0 17 21 1 0 0 0 0 17 23 1 6 0 0 0 18 19 2 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 20 24 2 0 0 0 0 21 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	375.2
Volume:	387.868
LogP:	2.835
LogD:	2.635
LogS:	-3.2
# Rotatable Bonds:	9
TPSA:	79.23
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.539
Synthetic Accessibility Score:	3.253
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.779
MDCK Permeability:	4.0237096982309595e-05
Pgp-inhibitor:	0.542
Pgp-substrate:	0.572
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.944
30% Bioavailability (F30%):	0.052

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.444
Plasma Protein Binding (PPB):	95.45955657958984%
Volume Distribution (VD):	1.003
Pgp-substrate:	4.387589454650879%

ADMET: Metabolism

CYP1A2-inhibitor:	0.561
CYP1A2-substrate:	0.51
CYP2C19-inhibitor:	0.545
CYP2C19-substrate:	0.521
CYP2C9-inhibitor:	0.39
CYP2C9-substrate:	0.781
CYP2D6-inhibitor:	0.92
CYP2D6-substrate:	0.351
CYP3A4-inhibitor:	0.933
CYP3A4-substrate:	0.184

ADMET: Excretion

Clearance (CL):	5.763
Half-life (T1/2):	0.496

ADMET: Toxicity

hERG Blockers:	0.288
Human Hepatotoxicity (H-HT):	0.101
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.451
Skin Sensitization:	0.941
Carcinogencity:	0.403
Eye Corrosion:	0.004
Eye Irritation:	0.107
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC270811

Natural Product ID:	NPC270811
*Common Name:**	(E,8R,9R)-9-(1,3-Benzodioxol-5-Yl)-8,9-Dihydroxy-1-Piperidin-1-Ylnon-2-En-1-One
IUPAC Name:	(E,8R,9R)-9-(1,3-benzodioxol-5-yl)-8,9-dihydroxy-1-piperidin-1-ylnon-2-en-1-one
Synonyms:
Standard InCHIKey:	UEJKTNXAIXCFSD-RLPYETMNSA-N
Standard InCHI:	InChI=1S/C21H29NO5/c23-17(21(25)16-10-11-18-19(14-16)27-15-26-18)8-4-1-2-5-9-20(24)22-12-6-3-7-13-22/h5,9-11,14,17,21,23,25H,1-4,6-8,12-13,15H2/b9-5+/t17-,21-/m1/s1
SMILES:	O[C@H](c1ccc2c(c1)OCO2)[C@@H](CCCC/C=C/C(=O)N1CCCCC1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2347641
PubChem CID:	71579732
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872768]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	fruits	n.a.	n.a.	PMID[20839888]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23434420]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26237	Piper longum	Species	Piperaceae	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
IC50	2
Others	3

Activity Type	# Activity
Organism	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.9	n.a.	PMID[502730]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	110000.0	nM	PMID[502730]
NPT27	Others	Unspecified		CC50	=	210000.0	nM	PMID[502730]

☑ 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 NPC270811 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	230
0.1-0.2	1130
0.2-0.3	3587
0.3-0.4	11605
0.4-0.5	7190
0.5-0.6	9310
0.6-0.7	7914
0.7-0.8	1697
0.8-0.85	16
0.85-0.9	16
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471073
0.9021	High Similarity	NPC252107
0.8951	High Similarity	NPC99078
0.8889	High Similarity	NPC220923
0.8881	High Similarity	NPC277042
0.8881	High Similarity	NPC136330
0.8881	High Similarity	NPC255817
0.8881	High Similarity	NPC196609
0.8881	High Similarity	NPC205178
0.8881	High Similarity	NPC73883
0.8881	High Similarity	NPC230698
0.8881	High Similarity	NPC251454
0.8811	High Similarity	NPC167096
0.8759	High Similarity	NPC470707
0.8699	High Similarity	NPC231572
0.863	High Similarity	NPC248505
0.863	High Similarity	NPC95366
0.8562	High Similarity	NPC145446
0.8562	High Similarity	NPC137172
0.8493	Intermediate Similarity	NPC96406
0.8435	Intermediate Similarity	NPC469808
0.8425	Intermediate Similarity	NPC94280
0.8425	Intermediate Similarity	NPC328419
0.8425	Intermediate Similarity	NPC45783
0.8425	Intermediate Similarity	NPC193673
0.8425	Intermediate Similarity	NPC103947
0.8425	Intermediate Similarity	NPC159150
0.8378	Intermediate Similarity	NPC225745
0.8367	Intermediate Similarity	NPC180647
0.8344	Intermediate Similarity	NPC169742
0.8289	Intermediate Similarity	NPC244338
0.8288	Intermediate Similarity	NPC217574
0.8098	Intermediate Similarity	NPC231198
0.8041	Intermediate Similarity	NPC318862
0.8026	Intermediate Similarity	NPC226005
0.8025	Intermediate Similarity	NPC4304
0.8013	Intermediate Similarity	NPC28641
0.8013	Intermediate Similarity	NPC194359
0.8012	Intermediate Similarity	NPC474475
0.8	Intermediate Similarity	NPC100566
0.8	Intermediate Similarity	NPC181653
0.8	Intermediate Similarity	NPC190332
0.7988	Intermediate Similarity	NPC35345
0.7964	Intermediate Similarity	NPC225597
0.7964	Intermediate Similarity	NPC477640
0.7964	Intermediate Similarity	NPC470739
0.7952	Intermediate Similarity	NPC475686
0.7952	Intermediate Similarity	NPC58766
0.7939	Intermediate Similarity	NPC329717
0.7929	Intermediate Similarity	NPC237044
0.7917	Intermediate Similarity	NPC2314
0.7895	Intermediate Similarity	NPC214036
0.7895	Intermediate Similarity	NPC254610
0.7895	Intermediate Similarity	NPC157554
0.7895	Intermediate Similarity	NPC37468
0.7895	Intermediate Similarity	NPC113236
0.7892	Intermediate Similarity	NPC252960
0.7885	Intermediate Similarity	NPC469978
0.7882	Intermediate Similarity	NPC474325
0.7881	Intermediate Similarity	NPC470881
0.7871	Intermediate Similarity	NPC140502
0.787	Intermediate Similarity	NPC304675
0.7867	Intermediate Similarity	NPC147616
0.7867	Intermediate Similarity	NPC471505
0.7867	Intermediate Similarity	NPC104077
0.7867	Intermediate Similarity	NPC106739
0.7867	Intermediate Similarity	NPC259742
0.7867	Intermediate Similarity	NPC219671
0.7844	Intermediate Similarity	NPC266176
0.7844	Intermediate Similarity	NPC82533
0.7844	Intermediate Similarity	NPC290759
0.7844	Intermediate Similarity	NPC158148
0.7836	Intermediate Similarity	NPC474745
0.7831	Intermediate Similarity	NPC476002
0.7829	Intermediate Similarity	NPC55040
0.7824	Intermediate Similarity	NPC474470
0.7821	Intermediate Similarity	NPC267414
0.7818	Intermediate Similarity	NPC218614
0.7818	Intermediate Similarity	NPC320104
0.7818	Intermediate Similarity	NPC59567
0.7815	Intermediate Similarity	NPC25821
0.7815	Intermediate Similarity	NPC6836
0.7805	Intermediate Similarity	NPC97072
0.7805	Intermediate Similarity	NPC215829
0.78	Intermediate Similarity	NPC248307
0.78	Intermediate Similarity	NPC65942
0.7798	Intermediate Similarity	NPC311991
0.7792	Intermediate Similarity	NPC100389
0.7785	Intermediate Similarity	NPC270849
0.7785	Intermediate Similarity	NPC26653
0.7778	Intermediate Similarity	NPC186418
0.7771	Intermediate Similarity	NPC297342
0.7771	Intermediate Similarity	NPC110063
0.7765	Intermediate Similarity	NPC187678
0.7765	Intermediate Similarity	NPC49353
0.7764	Intermediate Similarity	NPC223124
0.7748	Intermediate Similarity	NPC252833
0.7744	Intermediate Similarity	NPC59028
0.7744	Intermediate Similarity	NPC92191
0.7742	Intermediate Similarity	NPC202700
0.7733	Intermediate Similarity	NPC472024
0.7733	Intermediate Similarity	NPC80600
0.7722	Intermediate Similarity	NPC83743
0.7722	Intermediate Similarity	NPC34587
0.7722	Intermediate Similarity	NPC34927
0.7722	Intermediate Similarity	NPC262182
0.7722	Intermediate Similarity	NPC476382
0.7722	Intermediate Similarity	NPC252292
0.7722	Intermediate Similarity	NPC100998
0.7722	Intermediate Similarity	NPC287615
0.7722	Intermediate Similarity	NPC216819
0.7716	Intermediate Similarity	NPC478268
0.7712	Intermediate Similarity	NPC174191
0.7712	Intermediate Similarity	NPC18576
0.7712	Intermediate Similarity	NPC101624
0.7712	Intermediate Similarity	NPC135777
0.7712	Intermediate Similarity	NPC142547
0.7712	Intermediate Similarity	NPC184938
0.7707	Intermediate Similarity	NPC478239
0.7703	Intermediate Similarity	NPC218323
0.7702	Intermediate Similarity	NPC470934
0.7702	Intermediate Similarity	NPC188393
0.7701	Intermediate Similarity	NPC475981
0.7701	Intermediate Similarity	NPC474746
0.7692	Intermediate Similarity	NPC472711
0.7692	Intermediate Similarity	NPC186406
0.7688	Intermediate Similarity	NPC470088
0.7682	Intermediate Similarity	NPC219677
0.7682	Intermediate Similarity	NPC9912
0.7677	Intermediate Similarity	NPC156376
0.7667	Intermediate Similarity	NPC307110
0.7667	Intermediate Similarity	NPC166040
0.7667	Intermediate Similarity	NPC248355
0.7662	Intermediate Similarity	NPC471665
0.7662	Intermediate Similarity	NPC172818
0.7662	Intermediate Similarity	NPC25695
0.7662	Intermediate Similarity	NPC177035
0.7662	Intermediate Similarity	NPC52277
0.7662	Intermediate Similarity	NPC193528
0.7662	Intermediate Similarity	NPC471664
0.7662	Intermediate Similarity	NPC199459
0.7658	Intermediate Similarity	NPC232228
0.7654	Intermediate Similarity	NPC33256
0.7647	Intermediate Similarity	NPC135127
0.7647	Intermediate Similarity	NPC47181
0.7647	Intermediate Similarity	NPC35731
0.7647	Intermediate Similarity	NPC476411
0.7644	Intermediate Similarity	NPC116284
0.7644	Intermediate Similarity	NPC248642
0.7643	Intermediate Similarity	NPC157816
0.764	Intermediate Similarity	NPC223125
0.7636	Intermediate Similarity	NPC106786
0.7636	Intermediate Similarity	NPC111485
0.7636	Intermediate Similarity	NPC329640
0.7632	Intermediate Similarity	NPC97316
0.7632	Intermediate Similarity	NPC473924
0.7628	Intermediate Similarity	NPC210478
0.7625	Intermediate Similarity	NPC475959
0.7625	Intermediate Similarity	NPC232992
0.7614	Intermediate Similarity	NPC230098
0.7613	Intermediate Similarity	NPC126206
0.7613	Intermediate Similarity	NPC166184
0.7613	Intermediate Similarity	NPC474039
0.7613	Intermediate Similarity	NPC304152
0.76	Intermediate Similarity	NPC147247
0.76	Intermediate Similarity	NPC156576
0.76	Intermediate Similarity	NPC302378
0.76	Intermediate Similarity	NPC246974
0.76	Intermediate Similarity	NPC470084
0.7597	Intermediate Similarity	NPC214729
0.7597	Intermediate Similarity	NPC7018
0.7595	Intermediate Similarity	NPC470950
0.7595	Intermediate Similarity	NPC46092
0.7595	Intermediate Similarity	NPC185307
0.7595	Intermediate Similarity	NPC477898
0.7593	Intermediate Similarity	NPC474560
0.7593	Intermediate Similarity	NPC12854
0.759	Intermediate Similarity	NPC205167
0.759	Intermediate Similarity	NPC249274
0.759	Intermediate Similarity	NPC165797
0.7584	Intermediate Similarity	NPC40352
0.7584	Intermediate Similarity	NPC213711
0.7584	Intermediate Similarity	NPC473960
0.7582	Intermediate Similarity	NPC196937
0.7582	Intermediate Similarity	NPC58585
0.7582	Intermediate Similarity	NPC254398
0.7582	Intermediate Similarity	NPC112237
0.758	Intermediate Similarity	NPC471908
0.7578	Intermediate Similarity	NPC80732
0.7578	Intermediate Similarity	NPC261122
0.7578	Intermediate Similarity	NPC210611
0.7578	Intermediate Similarity	NPC182119
0.7578	Intermediate Similarity	NPC192763
0.7578	Intermediate Similarity	NPC199311
0.7578	Intermediate Similarity	NPC300262
0.7578	Intermediate Similarity	NPC215095
0.7578	Intermediate Similarity	NPC28651
0.7578	Intermediate Similarity	NPC201148
0.7578	Intermediate Similarity	NPC3460
0.7574	Intermediate Similarity	NPC57812

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 NPC270811 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	593
0.2-0.3	1087
0.3-0.4	2328
0.4-0.5	2567
0.5-0.6	1542
0.6-0.7	769
0.7-0.8	108
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8881	High Similarity	NPD2492	Phase 1
0.8065	Intermediate Similarity	NPD5297	Approved
0.795	Intermediate Similarity	NPD2978	Approved
0.795	Intermediate Similarity	NPD2977	Approved
0.7922	Intermediate Similarity	NPD4237	Approved
0.7922	Intermediate Similarity	NPD4236	Phase 3
0.7771	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5604	Discontinued
0.764	Intermediate Similarity	NPD4210	Discontinued
0.7622	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD5772	Approved
0.7622	Intermediate Similarity	NPD5773	Approved
0.758	Intermediate Similarity	NPD3060	Approved
0.758	Intermediate Similarity	NPD5177	Phase 3
0.7561	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD5582	Discontinued
0.7531	Intermediate Similarity	NPD3687	Approved
0.7531	Intermediate Similarity	NPD3686	Approved
0.7484	Intermediate Similarity	NPD2219	Phase 1
0.747	Intermediate Similarity	NPD2563	Approved
0.747	Intermediate Similarity	NPD2560	Approved
0.7452	Intermediate Similarity	NPD1375	Discontinued
0.7412	Intermediate Similarity	NPD6071	Discontinued
0.7397	Intermediate Similarity	NPD1357	Approved
0.7394	Intermediate Similarity	NPD6385	Approved
0.7394	Intermediate Similarity	NPD6386	Approved
0.7378	Intermediate Similarity	NPD824	Approved
0.7375	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2970	Approved
0.7368	Intermediate Similarity	NPD2969	Approved
0.7365	Intermediate Similarity	NPD3705	Approved
0.7362	Intermediate Similarity	NPD2122	Discontinued
0.7342	Intermediate Similarity	NPD7266	Discontinued
0.733	Intermediate Similarity	NPD7549	Discontinued
0.732	Intermediate Similarity	NPD3027	Phase 3
0.7317	Intermediate Similarity	NPD1653	Approved
0.731	Intermediate Similarity	NPD3051	Approved
0.729	Intermediate Similarity	NPD2238	Phase 2
0.7288	Intermediate Similarity	NPD7280	Phase 3
0.7288	Intermediate Similarity	NPD7281	Phase 3
0.7284	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4357	Discontinued
0.7273	Intermediate Similarity	NPD5718	Phase 2
0.7267	Intermediate Similarity	NPD5241	Discontinued
0.7255	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4162	Approved
0.7247	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3146	Approved
0.7239	Intermediate Similarity	NPD4123	Phase 3
0.7229	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD27	Approved
0.7225	Intermediate Similarity	NPD2489	Approved
0.7225	Intermediate Similarity	NPD2898	Approved
0.7222	Intermediate Similarity	NPD6842	Approved
0.7222	Intermediate Similarity	NPD6843	Phase 3
0.7222	Intermediate Similarity	NPD6841	Approved
0.7215	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2041	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2042	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7038	Approved
0.7175	Intermediate Similarity	NPD7039	Approved
0.7168	Intermediate Similarity	NPD2388	Discontinued
0.716	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5353	Approved
0.7159	Intermediate Similarity	NPD3885	Approved
0.7143	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4481	Phase 3
0.7115	Intermediate Similarity	NPD2674	Phase 3
0.7104	Intermediate Similarity	NPD7296	Approved
0.7097	Intermediate Similarity	NPD4420	Approved
0.7093	Intermediate Similarity	NPD2904	Discontinued
0.7089	Intermediate Similarity	NPD817	Approved
0.7089	Intermediate Similarity	NPD823	Approved
0.7086	Intermediate Similarity	NPD2233	Approved
0.7086	Intermediate Similarity	NPD2232	Approved
0.7086	Intermediate Similarity	NPD2230	Approved
0.7083	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4772	Phase 2
0.7083	Intermediate Similarity	NPD4773	Phase 2
0.7083	Intermediate Similarity	NPD7110	Phase 1
0.7076	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1774	Approved
0.7072	Intermediate Similarity	NPD4663	Approved
0.707	Intermediate Similarity	NPD3059	Approved
0.707	Intermediate Similarity	NPD3061	Approved
0.707	Intermediate Similarity	NPD3062	Approved
0.7059	Intermediate Similarity	NPD5978	Approved
0.7059	Intermediate Similarity	NPD5977	Approved
0.7055	Intermediate Similarity	NPD2677	Approved
0.7048	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3818	Discontinued
0.7044	Intermediate Similarity	NPD6896	Approved
0.7044	Intermediate Similarity	NPD6111	Discontinued
0.7044	Intermediate Similarity	NPD6895	Approved
0.7041	Intermediate Similarity	NPD3384	Approved
0.7041	Intermediate Similarity	NPD3383	Approved
0.7041	Intermediate Similarity	NPD3382	Approved
0.7041	Intermediate Similarity	NPD37	Approved
0.7039	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7906	Approved
0.703	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD3158	Phase 1
0.703	Intermediate Similarity	NPD3157	Approved
0.703	Intermediate Similarity	NPD3536	Discontinued
0.7024	Intermediate Similarity	NPD4675	Approved
0.7024	Intermediate Similarity	NPD4678	Approved
0.702	Intermediate Similarity	NPD1091	Approved
0.7019	Intermediate Similarity	NPD3656	Approved
0.7012	Intermediate Similarity	NPD5295	Discontinued
0.7012	Intermediate Similarity	NPD6667	Approved
0.7012	Intermediate Similarity	NPD7124	Phase 2
0.7012	Intermediate Similarity	NPD3122	Phase 3
0.7012	Intermediate Similarity	NPD6666	Approved
0.7	Intermediate Similarity	NPD2667	Approved
0.7	Intermediate Similarity	NPD7313	Approved
0.7	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2668	Approved
0.7	Intermediate Similarity	NPD4577	Approved
0.7	Intermediate Similarity	NPD4578	Approved
0.7	Intermediate Similarity	NPD7311	Approved
0.7	Intermediate Similarity	NPD7312	Approved
0.7	Intermediate Similarity	NPD7310	Approved
0.7	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6873	Phase 2
0.6981	Remote Similarity	NPD5314	Approved
0.6971	Remote Similarity	NPD5242	Approved
0.6962	Remote Similarity	NPD1613	Approved
0.6962	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7309	Approved
0.6957	Remote Similarity	NPD2161	Phase 2
0.6957	Remote Similarity	NPD6032	Approved
0.6957	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7047	Phase 3
0.6947	Remote Similarity	NPD5005	Approved
0.6947	Remote Similarity	NPD5006	Approved
0.6943	Remote Similarity	NPD3145	Approved
0.6943	Remote Similarity	NPD3144	Approved
0.694	Remote Similarity	NPD4157	Discontinued
0.6928	Remote Similarity	NPD4584	Approved
0.6928	Remote Similarity	NPD4739	Approved
0.6927	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6297	Approved
0.6923	Remote Similarity	NPD6875	Approved
0.6923	Remote Similarity	NPD6876	Approved
0.6919	Remote Similarity	NPD4965	Approved
0.6919	Remote Similarity	NPD4966	Approved
0.6919	Remote Similarity	NPD4967	Phase 2
0.6914	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4166	Phase 2
0.691	Remote Similarity	NPD5312	Approved
0.691	Remote Similarity	NPD5313	Approved
0.6902	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4666	Phase 3
0.689	Remote Similarity	NPD6331	Phase 2
0.6885	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5089	Approved
0.6882	Remote Similarity	NPD5090	Approved
0.6879	Remote Similarity	NPD3180	Approved
0.6879	Remote Similarity	NPD3179	Approved
0.6879	Remote Similarity	NPD8031	Discontinued
0.6875	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2653	Approved
0.6868	Remote Similarity	NPD6853	Approved
0.6868	Remote Similarity	NPD6851	Approved
0.6867	Remote Similarity	NPD7213	Phase 3
0.6867	Remote Similarity	NPD7212	Phase 2
0.6864	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD2235	Phase 2
0.6863	Remote Similarity	NPD2231	Phase 2
0.686	Remote Similarity	NPD2415	Discontinued
0.6855	Remote Similarity	NPD3140	Approved
0.6855	Remote Similarity	NPD3142	Approved
0.6854	Remote Similarity	NPD7177	Discontinued
0.6849	Remote Similarity	NPD228	Approved
0.6845	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD3641	Approved
0.6845	Remote Similarity	NPD4727	Phase 1
0.6845	Remote Similarity	NPD5976	Discontinued
0.6845	Remote Similarity	NPD3640	Phase 3
0.6845	Remote Similarity	NPD3639	Approved
0.6845	Remote Similarity	NPD1670	Discontinued
0.6842	Remote Similarity	NPD5457	Discontinued
0.6842	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6844	Discontinued
0.6839	Remote Similarity	NPD6234	Discontinued
0.6839	Remote Similarity	NPD5709	Phase 3
0.6836	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD597	Approved
0.6835	Remote Similarity	NPD598	Approved
0.6835	Remote Similarity	NPD601	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