NPASS Compound

Structure

NPC231767 OpenBabel07101719152D 25 27 0 0 1 0 0 0 0 0999 V2000 -2.7008 -2.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2235 -1.7945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7959 1.3689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5668 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3309 1.3288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6328 -1.6123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8347 -0.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0218 0.7935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8198 0.8836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8347 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7008 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4749 0.3730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5668 -0.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6330 0.8856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1796 -1.1919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3091 0.5353 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0462 -0.6164 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4328 -0.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6219 1.0347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6466 -1.7552 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4240 1.2155 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0350 -0.7655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9556 0.2948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 10 1 0 0 0 0 2 6 1 0 0 0 0 2 10 1 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 12 13 1 0 0 0 0 12 14 2 0 0 0 0 13 15 2 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 17 19 1 0 0 0 0 17 23 1 6 0 0 0 18 19 1 0 0 0 0 18 24 1 1 0 0 0 19 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.13
Volume:	345.797
LogP:	1.407
LogD:	0.869
LogS:	-2.894
# Rotatable Bonds:	0
TPSA:	118.22
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.485
Synthetic Accessibility Score:	5.452
Fsp3:	0.316
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:	-5.063
MDCK Permeability:	4.842121597903315e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.892
Human Intestinal Absorption (HIA):	0.059
20% Bioavailability (F20%):	0.899
30% Bioavailability (F30%):	0.759

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.131
Plasma Protein Binding (PPB):	93.86549377441406%
Volume Distribution (VD):	0.804
Pgp-substrate:	18.174163818359375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.369
CYP1A2-substrate:	0.065
CYP2C19-inhibitor:	0.089
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.751
CYP2D6-inhibitor:	0.319
CYP2D6-substrate:	0.502
CYP3A4-inhibitor:	0.06
CYP3A4-substrate:	0.103

ADMET: Excretion

Clearance (CL):	13.993
Half-life (T1/2):	0.682

ADMET: Toxicity

hERG Blockers:	0.112
Human Hepatotoxicity (H-HT):	0.337
Drug-inuced Liver Injury (DILI):	0.558
AMES Toxicity:	0.459
Rat Oral Acute Toxicity:	0.484
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.706
Carcinogencity:	0.06
Eye Corrosion:	0.003
Eye Irritation:	0.057
Respiratory Toxicity:	0.19

Download Data

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

Natural Product: NPC231767

Natural Product ID:	NPC231767
*Common Name:**	Carpinontriol B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HXRHVUWGMADGQP-FHWLQOOXSA-N
Standard InCHI:	InChI=1S/C19H20O6/c20-14-4-1-10-2-6-16(22)18(24)19(25)17(23)9-11-3-5-15(21)13(8-11)12(14)7-10/h1,3-5,7-8,17-21,23-25H,2,6,9H2/t17-,18-,19-/m0/s1
SMILES:	O=C1CCc2ccc(c(c2)c2cc(C[C@@H]([C@@H]([C@H]1O)O)O)ccc2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520000
PubChem CID:	11035325
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002652] Cyclic diarylheptanoids [CHEMONTID:0003524] Meta,meta-bridged biphenyls

*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
NPO12848	Carpinus cordata	Species	Betulaceae	Eukaryota	stems	n.a.	n.a.	PMID[12350169]
NPO12848	Carpinus cordata	Species	Betulaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	80.2	ug.mL-1	PMID[464232]

☑ 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 NPC231767 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	290
0.1-0.2	1194
0.2-0.3	3060
0.3-0.4	8486
0.4-0.5	11200
0.5-0.6	5245
0.6-0.7	10270
0.7-0.8	2844
0.8-0.85	85
0.85-0.9	14
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9748	High Similarity	NPC127975
0.9487	High Similarity	NPC182240
0.9412	High Similarity	NPC31936
0.9407	High Similarity	NPC473136
0.8889	High Similarity	NPC286222
0.8803	High Similarity	NPC308689
0.8803	High Similarity	NPC177576
0.8739	High Similarity	NPC473137
0.8718	High Similarity	NPC252544
0.8718	High Similarity	NPC321252
0.8718	High Similarity	NPC44732
0.8618	High Similarity	NPC265454
0.8618	High Similarity	NPC34634
0.8607	High Similarity	NPC104514
0.8583	High Similarity	NPC285350
0.8583	High Similarity	NPC12656
0.8547	High Similarity	NPC262365
0.8421	Intermediate Similarity	NPC70859
0.8421	Intermediate Similarity	NPC130899
0.8421	Intermediate Similarity	NPC61153
0.8421	Intermediate Similarity	NPC283590
0.8413	Intermediate Similarity	NPC86900
0.84	Intermediate Similarity	NPC98305
0.839	Intermediate Similarity	NPC317305
0.8361	Intermediate Similarity	NPC23402
0.8281	Intermediate Similarity	NPC474803
0.8279	Intermediate Similarity	NPC221870
0.8271	Intermediate Similarity	NPC139074
0.8271	Intermediate Similarity	NPC213485
0.8271	Intermediate Similarity	NPC40524
0.8258	Intermediate Similarity	NPC108553
0.822	Intermediate Similarity	NPC188677
0.8205	Intermediate Similarity	NPC261573
0.8205	Intermediate Similarity	NPC8931
0.8205	Intermediate Similarity	NPC120693
0.8205	Intermediate Similarity	NPC288411
0.8203	Intermediate Similarity	NPC198014
0.8195	Intermediate Similarity	NPC17843
0.8189	Intermediate Similarity	NPC295034
0.8168	Intermediate Similarity	NPC158673
0.8167	Intermediate Similarity	NPC326187
0.816	Intermediate Similarity	NPC249435
0.8151	Intermediate Similarity	NPC228737
0.814	Intermediate Similarity	NPC181334
0.8136	Intermediate Similarity	NPC138942
0.8134	Intermediate Similarity	NPC314048
0.8125	Intermediate Similarity	NPC469927
0.812	Intermediate Similarity	NPC475042
0.812	Intermediate Similarity	NPC476407
0.812	Intermediate Similarity	NPC168829
0.8115	Intermediate Similarity	NPC228988
0.811	Intermediate Similarity	NPC164852
0.811	Intermediate Similarity	NPC216216
0.8106	Intermediate Similarity	NPC474546
0.8106	Intermediate Similarity	NPC102829
0.8106	Intermediate Similarity	NPC120488
0.8095	Intermediate Similarity	NPC473767
0.8085	Intermediate Similarity	NPC474799
0.8077	Intermediate Similarity	NPC87985
0.8067	Intermediate Similarity	NPC70843
0.8062	Intermediate Similarity	NPC471187
0.8045	Intermediate Similarity	NPC17968
0.8045	Intermediate Similarity	NPC470122
0.8045	Intermediate Similarity	NPC469705
0.8034	Intermediate Similarity	NPC91461
0.8034	Intermediate Similarity	NPC7686
0.8034	Intermediate Similarity	NPC40258
0.8031	Intermediate Similarity	NPC7151
0.8031	Intermediate Similarity	NPC216297
0.8031	Intermediate Similarity	NPC473662
0.8031	Intermediate Similarity	NPC223451
0.803	Intermediate Similarity	NPC767
0.803	Intermediate Similarity	NPC247250
0.803	Intermediate Similarity	NPC217431
0.8017	Intermediate Similarity	NPC88141
0.8016	Intermediate Similarity	NPC184527
0.8015	Intermediate Similarity	NPC71610
0.8	Intermediate Similarity	NPC74507
0.8	Intermediate Similarity	NPC152525
0.8	Intermediate Similarity	NPC68756
0.8	Intermediate Similarity	NPC85310
0.8	Intermediate Similarity	NPC234890
0.8	Intermediate Similarity	NPC471749
0.8	Intermediate Similarity	NPC52407
0.7985	Intermediate Similarity	NPC85342
0.7984	Intermediate Similarity	NPC176208
0.7971	Intermediate Similarity	NPC175552
0.7971	Intermediate Similarity	NPC206207
0.7951	Intermediate Similarity	NPC21162
0.7949	Intermediate Similarity	NPC213730
0.7943	Intermediate Similarity	NPC148545
0.7926	Intermediate Similarity	NPC478190
0.7926	Intermediate Similarity	NPC471066
0.7926	Intermediate Similarity	NPC471095
0.7923	Intermediate Similarity	NPC236981
0.792	Intermediate Similarity	NPC474486
0.7917	Intermediate Similarity	NPC29989
0.7917	Intermediate Similarity	NPC95178
0.7917	Intermediate Similarity	NPC69332
0.791	Intermediate Similarity	NPC199253
0.791	Intermediate Similarity	NPC137427
0.791	Intermediate Similarity	NPC244246
0.791	Intermediate Similarity	NPC319282
0.791	Intermediate Similarity	NPC215941
0.791	Intermediate Similarity	NPC123196
0.791	Intermediate Similarity	NPC311419
0.791	Intermediate Similarity	NPC275724
0.791	Intermediate Similarity	NPC65935
0.791	Intermediate Similarity	NPC136588
0.7907	Intermediate Similarity	NPC196976
0.7899	Intermediate Similarity	NPC67349
0.7899	Intermediate Similarity	NPC170742
0.7899	Intermediate Similarity	NPC279676
0.7895	Intermediate Similarity	NPC48248
0.7887	Intermediate Similarity	NPC244691
0.7887	Intermediate Similarity	NPC245482
0.7887	Intermediate Similarity	NPC474982
0.7887	Intermediate Similarity	NPC301751
0.7887	Intermediate Similarity	NPC79627
0.7887	Intermediate Similarity	NPC471906
0.7886	Intermediate Similarity	NPC257430
0.7886	Intermediate Similarity	NPC187583
0.7886	Intermediate Similarity	NPC179002
0.7883	Intermediate Similarity	NPC103082
0.7883	Intermediate Similarity	NPC158325
0.7883	Intermediate Similarity	NPC103398
0.7883	Intermediate Similarity	NPC180171
0.7883	Intermediate Similarity	NPC152209
0.7879	Intermediate Similarity	NPC267846
0.7872	Intermediate Similarity	NPC469520
0.7872	Intermediate Similarity	NPC474961
0.7868	Intermediate Similarity	NPC164172
0.7863	Intermediate Similarity	NPC132078
0.7863	Intermediate Similarity	NPC51333
0.7863	Intermediate Similarity	NPC216468
0.7863	Intermediate Similarity	NPC78119
0.7857	Intermediate Similarity	NPC299252
0.7857	Intermediate Similarity	NPC28951
0.7857	Intermediate Similarity	NPC325646
0.7857	Intermediate Similarity	NPC61062
0.7857	Intermediate Similarity	NPC136649
0.7857	Intermediate Similarity	NPC277394
0.7852	Intermediate Similarity	NPC244699
0.7852	Intermediate Similarity	NPC93015
0.7842	Intermediate Similarity	NPC141368
0.784	Intermediate Similarity	NPC473931
0.784	Intermediate Similarity	NPC474050
0.784	Intermediate Similarity	NPC474114
0.7836	Intermediate Similarity	NPC474998
0.7829	Intermediate Similarity	NPC32322
0.7829	Intermediate Similarity	NPC259703
0.7826	Intermediate Similarity	NPC475549
0.7823	Intermediate Similarity	NPC48525
0.7823	Intermediate Similarity	NPC228425
0.782	Intermediate Similarity	NPC169250
0.782	Intermediate Similarity	NPC72158
0.782	Intermediate Similarity	NPC100067
0.782	Intermediate Similarity	NPC116513
0.782	Intermediate Similarity	NPC190043
0.782	Intermediate Similarity	NPC30501
0.782	Intermediate Similarity	NPC266689
0.782	Intermediate Similarity	NPC30491
0.782	Intermediate Similarity	NPC262936
0.782	Intermediate Similarity	NPC105157
0.782	Intermediate Similarity	NPC103356
0.782	Intermediate Similarity	NPC162612
0.782	Intermediate Similarity	NPC23126
0.782	Intermediate Similarity	NPC98254
0.7812	Intermediate Similarity	NPC151197
0.781	Intermediate Similarity	NPC282780
0.781	Intermediate Similarity	NPC166480
0.7805	Intermediate Similarity	NPC120982
0.7805	Intermediate Similarity	NPC174096
0.7805	Intermediate Similarity	NPC475018
0.7805	Intermediate Similarity	NPC226401
0.7805	Intermediate Similarity	NPC79793
0.7805	Intermediate Similarity	NPC63345
0.7805	Intermediate Similarity	NPC147634
0.7805	Intermediate Similarity	NPC296683
0.7803	Intermediate Similarity	NPC477213
0.7801	Intermediate Similarity	NPC91019
0.7801	Intermediate Similarity	NPC106519
0.7801	Intermediate Similarity	NPC187843
0.7795	Intermediate Similarity	NPC76308
0.7795	Intermediate Similarity	NPC325295
0.7794	Intermediate Similarity	NPC246693
0.7794	Intermediate Similarity	NPC242358
0.7794	Intermediate Similarity	NPC70622
0.7794	Intermediate Similarity	NPC110609
0.7786	Intermediate Similarity	NPC179505
0.7786	Intermediate Similarity	NPC156709
0.7786	Intermediate Similarity	NPC256162
0.7786	Intermediate Similarity	NPC59775
0.7778	Intermediate Similarity	NPC147757
0.7778	Intermediate Similarity	NPC31799
0.7778	Intermediate Similarity	NPC322197
0.7778	Intermediate Similarity	NPC244441
0.7778	Intermediate Similarity	NPC136878
0.7778	Intermediate Similarity	NPC316769
0.7778	Intermediate Similarity	NPC285122

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 NPC231767 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	267
0.1-0.2	827
0.2-0.3	1426
0.3-0.4	2696
0.4-0.5	2124
0.5-0.6	1170
0.6-0.7	576
0.7-0.8	64
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
0.7929	Intermediate Similarity	NPD3400	Discontinued
0.7803	Intermediate Similarity	NPD1164	Approved
0.7609	Intermediate Similarity	NPD6355	Discontinued
0.7568	Intermediate Similarity	NPD4380	Phase 2
0.7563	Intermediate Similarity	NPD3020	Approved
0.7537	Intermediate Similarity	NPD1470	Approved
0.7536	Intermediate Similarity	NPD943	Approved
0.7518	Intermediate Similarity	NPD6798	Discontinued
0.7518	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD1201	Approved
0.7481	Intermediate Similarity	NPD2932	Approved
0.7481	Intermediate Similarity	NPD3019	Approved
0.7466	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD2860	Approved
0.7458	Intermediate Similarity	NPD2859	Approved
0.744	Intermediate Similarity	NPD3021	Approved
0.744	Intermediate Similarity	NPD3022	Approved
0.741	Intermediate Similarity	NPD4060	Phase 1
0.7394	Intermediate Similarity	NPD5405	Approved
0.7394	Intermediate Similarity	NPD5408	Approved
0.7394	Intermediate Similarity	NPD5406	Approved
0.7394	Intermediate Similarity	NPD5404	Approved
0.7373	Intermediate Similarity	NPD2934	Approved
0.7373	Intermediate Similarity	NPD2933	Approved
0.7338	Intermediate Similarity	NPD6233	Phase 2
0.7324	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD2799	Discontinued
0.7324	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1237	Approved
0.7308	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD2629	Approved
0.7279	Intermediate Similarity	NPD3094	Phase 2
0.7279	Intermediate Similarity	NPD7390	Discontinued
0.7273	Intermediate Similarity	NPD7075	Discontinued
0.7273	Intermediate Similarity	NPD1651	Approved
0.7273	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD7635	Approved
0.726	Intermediate Similarity	NPD6190	Approved
0.7211	Intermediate Similarity	NPD3300	Phase 2
0.7203	Intermediate Similarity	NPD1510	Phase 2
0.719	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD9495	Approved
0.7172	Intermediate Similarity	NPD2424	Discontinued
0.7167	Intermediate Similarity	NPD1809	Phase 2
0.7143	Intermediate Similarity	NPD845	Approved
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD2342	Discontinued
0.7124	Intermediate Similarity	NPD6801	Discontinued
0.7111	Intermediate Similarity	NPD3092	Approved
0.7103	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2344	Approved
0.7092	Intermediate Similarity	NPD6663	Approved
0.7092	Intermediate Similarity	NPD4062	Phase 3
0.7083	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1283	Approved
0.7078	Intermediate Similarity	NPD8455	Phase 2
0.7077	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD3091	Approved
0.7055	Intermediate Similarity	NPD1549	Phase 2
0.7054	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD5736	Approved
0.7042	Intermediate Similarity	NPD1240	Approved
0.7037	Intermediate Similarity	NPD3026	Approved
0.7037	Intermediate Similarity	NPD3023	Approved
0.7032	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD940	Approved
0.7016	Intermediate Similarity	NPD846	Approved
0.7015	Intermediate Similarity	NPD3024	Approved
0.7015	Intermediate Similarity	NPD3025	Approved
0.7013	Intermediate Similarity	NPD1934	Approved
0.7007	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6166	Phase 2
0.7	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD3882	Suspended
0.6981	Remote Similarity	NPD3787	Discontinued
0.6978	Remote Similarity	NPD2798	Approved
0.6978	Remote Similarity	NPD5647	Approved
0.6972	Remote Similarity	NPD6405	Approved
0.6972	Remote Similarity	NPD6407	Approved
0.6966	Remote Similarity	NPD7033	Discontinued
0.6959	Remote Similarity	NPD4628	Phase 3
0.6959	Remote Similarity	NPD8166	Discontinued
0.6954	Remote Similarity	NPD1512	Approved
0.6953	Remote Similarity	NPD74	Approved
0.6953	Remote Similarity	NPD9266	Approved
0.695	Remote Similarity	NPD3027	Phase 3
0.6944	Remote Similarity	NPD1607	Approved
0.6939	Remote Similarity	NPD5958	Discontinued
0.6939	Remote Similarity	NPD4534	Discontinued
0.6935	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6799	Approved
0.6923	Remote Similarity	NPD2979	Phase 3
0.6923	Remote Similarity	NPD5402	Approved
0.6918	Remote Similarity	NPD4477	Approved
0.6918	Remote Similarity	NPD9570	Approved
0.6918	Remote Similarity	NPD4476	Approved
0.6918	Remote Similarity	NPD2438	Suspended
0.6917	Remote Similarity	NPD9493	Approved
0.6913	Remote Similarity	NPD2309	Approved
0.6908	Remote Similarity	NPD5403	Approved
0.6906	Remote Similarity	NPD2797	Approved
0.6901	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3268	Approved
0.6901	Remote Similarity	NPD3764	Approved
0.6892	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD844	Approved
0.6884	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6599	Discontinued
0.6879	Remote Similarity	NPD7768	Phase 2
0.6875	Remote Similarity	NPD6232	Discontinued
0.6875	Remote Similarity	NPD9264	Approved
0.6875	Remote Similarity	NPD9267	Approved
0.6875	Remote Similarity	NPD9263	Approved
0.6871	Remote Similarity	NPD6004	Phase 3
0.6871	Remote Similarity	NPD2346	Discontinued
0.6871	Remote Similarity	NPD6002	Phase 3
0.6871	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6005	Phase 3
0.6871	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD1281	Approved
0.6861	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD1535	Discovery
0.6859	Remote Similarity	NPD2801	Approved
0.6852	Remote Similarity	NPD7473	Discontinued
0.685	Remote Similarity	NPD5048	Discontinued
0.6848	Remote Similarity	NPD6559	Discontinued
0.6846	Remote Similarity	NPD7003	Approved
0.6838	Remote Similarity	NPD3095	Discontinued
0.6838	Remote Similarity	NPD4589	Approved
0.6831	Remote Similarity	NPD7095	Approved
0.6829	Remote Similarity	NPD288	Approved
0.6825	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1511	Approved
0.6818	Remote Similarity	NPD7458	Discontinued
0.6818	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5303	Approved
0.6815	Remote Similarity	NPD1894	Discontinued
0.6815	Remote Similarity	NPD1759	Phase 1
0.6815	Remote Similarity	NPD5304	Approved
0.6813	Remote Similarity	NPD6959	Discontinued
0.6812	Remote Similarity	NPD1481	Phase 2
0.681	Remote Similarity	NPD3751	Discontinued
0.681	Remote Similarity	NPD3818	Discontinued
0.6809	Remote Similarity	NPD2861	Phase 2
0.6809	Remote Similarity	NPD4208	Discontinued
0.6806	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD1613	Approved
0.6803	Remote Similarity	NPD2796	Approved
0.68	Remote Similarity	NPD1242	Phase 1
0.6795	Remote Similarity	NPD37	Approved
0.6788	Remote Similarity	NPD3847	Discontinued
0.6786	Remote Similarity	NPD1203	Approved
0.6779	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5401	Approved
0.6776	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD4750	Phase 3
0.6766	Remote Similarity	NPD5035	Approved
0.6761	Remote Similarity	NPD4908	Phase 1
0.6752	Remote Similarity	NPD7819	Suspended
0.6746	Remote Similarity	NPD8150	Discontinued
0.6741	Remote Similarity	NPD1758	Phase 1
0.6739	Remote Similarity	NPD1610	Phase 2
0.6738	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD6085	Phase 2
0.6733	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD3750	Approved
0.6731	Remote Similarity	NPD7411	Suspended
0.6731	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD256	Approved
0.6716	Remote Similarity	NPD7157	Approved
0.6716	Remote Similarity	NPD255	Approved
0.6715	Remote Similarity	NPD4626	Approved
0.6715	Remote Similarity	NPD2286	Discontinued
0.6715	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3817	Phase 2
0.6707	Remote Similarity	NPD5026	Approved
0.6707	Remote Similarity	NPD5034	Approved
0.6707	Remote Similarity	NPD36	Approved
0.6707	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5028	Approved
0.6707	Remote Similarity	NPD4955	Approved
0.6707	Remote Similarity	NPD4954	Approved
0.6692	Remote Similarity	NPD2234	Approved
0.6692	Remote Similarity	NPD2684	Approved
0.6692	Remote Similarity	NPD2229	Approved
0.6692	Remote Similarity	NPD2228	Approved
0.6691	Remote Similarity	NPD3972	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