NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	464.26
Volume:	498.774
LogP:	4.26
LogD:	3.952
LogS:	-4.874
# Rotatable Bonds:	4
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.391
Synthetic Accessibility Score:	5.341
Fsp3:	0.517
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.815
MDCK Permeability:	2.5201910830219276e-05
Pgp-inhibitor:	0.972
Pgp-substrate:	0.282
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.053
30% Bioavailability (F30%):	0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	96.43163299560547%
Volume Distribution (VD):	1.516
Pgp-substrate:	3.4923574924468994%

ADMET: Metabolism

CYP1A2-inhibitor:	0.198
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.417
CYP2C19-substrate:	0.28
CYP2C9-inhibitor:	0.781
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.273
CYP2D6-substrate:	0.31
CYP3A4-inhibitor:	0.936
CYP3A4-substrate:	0.463

ADMET: Excretion

Clearance (CL):	9.679
Half-life (T1/2):	0.17

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.487
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.952
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.052
Carcinogencity:	0.232
Eye Corrosion:	0.004
Eye Irritation:	0.025
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC477370

Natural Product ID:	NPC477370
*Common Name:**	[(1R,3E,5S,7S,11R,12R,13S,14S)-11,13-dihydroxy-3,6,6,14-tetramethyl-10-methylidene-2-oxo-1-tricyclo[10.3.0.05,7]pentadec-3-enyl] (E)-3-phenylprop-2-enoate
IUPAC Name:	[(1R,3E,5S,7S,11R,12R,13S,14S)-11,13-dihydroxy-3,6,6,14-tetramethyl-10-methylidene-2-oxo-1-tricyclo[10.3.0.05,7]pentadec-3-enyl] (E)-3-phenylprop-2-enoate
Synonyms:
Standard InCHIKey:	SXGKGXOUXRBQMQ-DPAOASNOSA-N
Standard InCHI:	InChI=1S/C29H36O5/c1-17-11-13-21-22(28(21,4)5)15-18(2)27(33)29(16-19(3)26(32)24(29)25(17)31)34-23(30)14-12-20-9-7-6-8-10-20/h6-10,12,14-15,19,21-22,24-26,31-32H,1,11,13,16H2,2-5H3/b14-12+,18-15+/t19-,21-,22-,24-,25-,26-,29+/m0/s1
SMILES:	C[C@H]1C[C@]2([C@H]([C@H]1O)[C@H](C(=C)CC[C@H]3[C@@H](C3(C)C)/C=C(/C2=O)\C)O)OC(=O)/C=C/C4=CC=CC=C4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	56669872
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO28682	Jatropha multifida	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19036584]
NPO28682	Jatropha multifida	Species	Euphorbiaceae	Eukaryota	stems	Botanical Garden, Osmania University, Hyderabad, Andhra Pradesh	2006-AUG	PMID[21534583]
NPO28682	Jatropha multifida	Species	Euphorbiaceae	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	1

Activity Type	# Activity
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	<	30	%	PMID[21534583]

☑ 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 NPC477370 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	256
0.1-0.2	899
0.2-0.3	2138
0.3-0.4	5988
0.4-0.5	11451
0.5-0.6	17192
0.6-0.7	4342
0.7-0.8	291
0.8-0.85	94
0.85-0.9	23
0.9-0.95	12
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9917	High Similarity	NPC477365
0.9833	High Similarity	NPC477363
0.9833	High Similarity	NPC477366
0.9754	High Similarity	NPC37968
0.9667	High Similarity	NPC477362
0.959	High Similarity	NPC477357
0.9504	High Similarity	NPC8990
0.9449	High Similarity	NPC232888
0.9449	High Similarity	NPC477367
0.9426	High Similarity	NPC477369
0.937	High Similarity	NPC477368
0.9291	High Similarity	NPC477364
0.907	High Similarity	NPC477359
0.9055	High Similarity	NPC475671
0.9055	High Similarity	NPC42234
0.9055	High Similarity	NPC475452
0.8915	High Similarity	NPC477360
0.8906	High Similarity	NPC272946
0.8712	High Similarity	NPC472247
0.8712	High Similarity	NPC270364
0.8647	High Similarity	NPC477358
0.8571	High Similarity	NPC477099
0.8571	High Similarity	NPC477101
0.8571	High Similarity	NPC477097
0.8551	High Similarity	NPC471162
0.8529	High Similarity	NPC473497
0.8519	High Similarity	NPC276652
0.8473	Intermediate Similarity	NPC3450
0.8473	Intermediate Similarity	NPC122504
0.8433	Intermediate Similarity	NPC290833
0.8433	Intermediate Similarity	NPC265459
0.8433	Intermediate Similarity	NPC475262
0.8406	Intermediate Similarity	NPC45307
0.8406	Intermediate Similarity	NPC153214
0.8394	Intermediate Similarity	NPC475413
0.8394	Intermediate Similarity	NPC474303
0.8394	Intermediate Similarity	NPC473654
0.8392	Intermediate Similarity	NPC477098
0.8392	Intermediate Similarity	NPC477100
0.837	Intermediate Similarity	NPC285221
0.837	Intermediate Similarity	NPC194769
0.8358	Intermediate Similarity	NPC472250
0.8346	Intermediate Similarity	NPC233692
0.831	Intermediate Similarity	NPC232583
0.831	Intermediate Similarity	NPC125033
0.831	Intermediate Similarity	NPC25484
0.8309	Intermediate Similarity	NPC86772
0.8298	Intermediate Similarity	NPC205389
0.8273	Intermediate Similarity	NPC477096
0.8273	Intermediate Similarity	NPC477094
0.8248	Intermediate Similarity	NPC272523
0.8248	Intermediate Similarity	NPC325805
0.8227	Intermediate Similarity	NPC170668
0.8222	Intermediate Similarity	NPC311492
0.8222	Intermediate Similarity	NPC28836
0.8209	Intermediate Similarity	NPC239358
0.8188	Intermediate Similarity	NPC251294
0.8188	Intermediate Similarity	NPC475660
0.8148	Intermediate Similarity	NPC472248
0.8143	Intermediate Similarity	NPC82467
0.8129	Intermediate Similarity	NPC242355
0.8102	Intermediate Similarity	NPC217673
0.8102	Intermediate Similarity	NPC52523
0.8102	Intermediate Similarity	NPC202729
0.8099	Intermediate Similarity	NPC477095
0.8074	Intermediate Similarity	NPC233860
0.8047	Intermediate Similarity	NPC472708
0.8043	Intermediate Similarity	NPC27721
0.8029	Intermediate Similarity	NPC200154
0.8029	Intermediate Similarity	NPC79699
0.7986	Intermediate Similarity	NPC473301
0.797	Intermediate Similarity	NPC472706
0.7929	Intermediate Similarity	NPC473440
0.791	Intermediate Similarity	NPC472707
0.7879	Intermediate Similarity	NPC140118
0.7879	Intermediate Similarity	NPC12881
0.7833	Intermediate Similarity	NPC118405
0.7826	Intermediate Similarity	NPC470143
0.7826	Intermediate Similarity	NPC322503
0.7817	Intermediate Similarity	NPC140021
0.7817	Intermediate Similarity	NPC183540
0.7794	Intermediate Similarity	NPC475508
0.7787	Intermediate Similarity	NPC321670
0.7778	Intermediate Similarity	NPC25043
0.7778	Intermediate Similarity	NPC134131
0.7746	Intermediate Similarity	NPC187566
0.7744	Intermediate Similarity	NPC472704
0.7734	Intermediate Similarity	NPC9274
0.7703	Intermediate Similarity	NPC22571
0.7703	Intermediate Similarity	NPC138641
0.7703	Intermediate Similarity	NPC283875
0.7703	Intermediate Similarity	NPC469648
0.7703	Intermediate Similarity	NPC469647
0.7698	Intermediate Similarity	NPC153617
0.7698	Intermediate Similarity	NPC471911
0.7698	Intermediate Similarity	NPC4242
0.7698	Intermediate Similarity	NPC329913
0.7698	Intermediate Similarity	NPC126516
0.7692	Intermediate Similarity	NPC63737
0.7669	Intermediate Similarity	NPC472703
0.7667	Intermediate Similarity	NPC70344
0.7664	Intermediate Similarity	NPC49272
0.7661	Intermediate Similarity	NPC20485
0.7655	Intermediate Similarity	NPC301946
0.7655	Intermediate Similarity	NPC277053
0.7639	Intermediate Similarity	NPC95449
0.7635	Intermediate Similarity	NPC472398
0.763	Intermediate Similarity	NPC476599
0.7626	Intermediate Similarity	NPC15850
0.7619	Intermediate Similarity	NPC477247
0.7612	Intermediate Similarity	NPC471466
0.7606	Intermediate Similarity	NPC170718
0.76	Intermediate Similarity	NPC469456
0.7586	Intermediate Similarity	NPC80895
0.7586	Intermediate Similarity	NPC471912
0.7584	Intermediate Similarity	NPC145649
0.7584	Intermediate Similarity	NPC233581
0.7576	Intermediate Similarity	NPC475827
0.7576	Intermediate Similarity	NPC474223
0.7576	Intermediate Similarity	NPC473243
0.7574	Intermediate Similarity	NPC169913
0.7571	Intermediate Similarity	NPC298547
0.7571	Intermediate Similarity	NPC134937
0.7571	Intermediate Similarity	NPC324898
0.7571	Intermediate Similarity	NPC203486
0.755	Intermediate Similarity	NPC11410
0.7536	Intermediate Similarity	NPC82712
0.7536	Intermediate Similarity	NPC472388
0.7535	Intermediate Similarity	NPC184109
0.7532	Intermediate Similarity	NPC165234
0.7532	Intermediate Similarity	NPC475536
0.7532	Intermediate Similarity	NPC55744
0.7518	Intermediate Similarity	NPC279637
0.7518	Intermediate Similarity	NPC51448
0.7518	Intermediate Similarity	NPC115797
0.7518	Intermediate Similarity	NPC149401
0.7517	Intermediate Similarity	NPC284957
0.7517	Intermediate Similarity	NPC161955
0.75	Intermediate Similarity	NPC275576
0.75	Intermediate Similarity	NPC471862
0.75	Intermediate Similarity	NPC87090
0.75	Intermediate Similarity	NPC204784
0.7484	Intermediate Similarity	NPC475437
0.7484	Intermediate Similarity	NPC475464
0.7484	Intermediate Similarity	NPC473641
0.7484	Intermediate Similarity	NPC475505
0.7484	Intermediate Similarity	NPC473797
0.7484	Intermediate Similarity	NPC475300
0.7483	Intermediate Similarity	NPC9905
0.7483	Intermediate Similarity	NPC471176
0.7482	Intermediate Similarity	NPC72915
0.7467	Intermediate Similarity	NPC240592
0.7467	Intermediate Similarity	NPC117346
0.7464	Intermediate Similarity	NPC225103
0.7459	Intermediate Similarity	NPC477356
0.7452	Intermediate Similarity	NPC161151
0.7448	Intermediate Similarity	NPC51181
0.7448	Intermediate Similarity	NPC182869
0.7447	Intermediate Similarity	NPC477281
0.7447	Intermediate Similarity	NPC477280
0.7447	Intermediate Similarity	NPC19719
0.7444	Intermediate Similarity	NPC475804
0.7444	Intermediate Similarity	NPC474222
0.744	Intermediate Similarity	NPC477251
0.7432	Intermediate Similarity	NPC132652
0.7431	Intermediate Similarity	NPC87934
0.7431	Intermediate Similarity	NPC79921
0.7431	Intermediate Similarity	NPC162613
0.7429	Intermediate Similarity	NPC80599
0.7422	Intermediate Similarity	NPC477250
0.7415	Intermediate Similarity	NPC478264
0.7413	Intermediate Similarity	NPC327511
0.7413	Intermediate Similarity	NPC205305
0.741	Intermediate Similarity	NPC475138
0.741	Intermediate Similarity	NPC473443
0.7407	Intermediate Similarity	NPC474254
0.7407	Intermediate Similarity	NPC474159
0.74	Intermediate Similarity	NPC471103
0.7397	Intermediate Similarity	NPC131966
0.7397	Intermediate Similarity	NPC477894
0.7397	Intermediate Similarity	NPC191387
0.7394	Intermediate Similarity	NPC477893
0.7394	Intermediate Similarity	NPC477896
0.7391	Intermediate Similarity	NPC58061
0.7376	Intermediate Similarity	NPC323379
0.7376	Intermediate Similarity	NPC327204
0.7372	Intermediate Similarity	NPC79608
0.7368	Intermediate Similarity	NPC132599
0.7368	Intermediate Similarity	NPC473670
0.7368	Intermediate Similarity	NPC21410
0.7368	Intermediate Similarity	NPC251139
0.7368	Intermediate Similarity	NPC473632
0.7368	Intermediate Similarity	NPC469730
0.7365	Intermediate Similarity	NPC478263
0.7364	Intermediate Similarity	NPC287055
0.7364	Intermediate Similarity	NPC242957
0.7364	Intermediate Similarity	NPC477245
0.7364	Intermediate Similarity	NPC477246
0.7364	Intermediate Similarity	NPC306977
0.7364	Intermediate Similarity	NPC206414

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 NPC477370 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	693
0.2-0.3	1721
0.3-0.4	3048
0.4-0.5	2186
0.5-0.6	1057
0.6-0.7	217
0.7-0.8	15
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
0.8156	Intermediate Similarity	NPD7236	Approved
0.7917	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD7239	Suspended
0.7869	Intermediate Similarity	NPD6685	Approved
0.7769	Intermediate Similarity	NPD6647	Phase 2
0.7754	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD5765	Approved
0.754	Intermediate Similarity	NPD2067	Discontinued
0.7445	Intermediate Similarity	NPD6085	Phase 2
0.7445	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7961	Discontinued
0.7422	Intermediate Similarity	NPD6912	Phase 3
0.7403	Intermediate Similarity	NPD7057	Phase 3
0.7403	Intermediate Similarity	NPD7058	Phase 2
0.7364	Intermediate Similarity	NPD6858	Approved
0.7364	Intermediate Similarity	NPD7094	Approved
0.7259	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD2629	Approved
0.7172	Intermediate Similarity	NPD7305	Phase 1
0.7099	Intermediate Similarity	NPD7799	Discontinued
0.7077	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD5909	Discontinued
0.6967	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6002	Phase 3
0.6959	Remote Similarity	NPD6005	Phase 3
0.6959	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6004	Phase 3
0.6953	Remote Similarity	NPD5048	Discontinued
0.694	Remote Similarity	NPD4198	Discontinued
0.6923	Remote Similarity	NPD2182	Approved
0.6918	Remote Similarity	NPD6653	Approved
0.6917	Remote Similarity	NPD6010	Discontinued
0.6912	Remote Similarity	NPD7741	Discontinued
0.6892	Remote Similarity	NPD7137	Phase 2
0.6879	Remote Similarity	NPD6362	Approved
0.6846	Remote Similarity	NPD6899	Approved
0.6846	Remote Similarity	NPD6881	Approved
0.6831	Remote Similarity	NPD5647	Approved
0.6828	Remote Similarity	NPD6663	Approved
0.6825	Remote Similarity	NPD2066	Phase 3
0.6818	Remote Similarity	NPD6649	Approved
0.6818	Remote Similarity	NPD6650	Approved
0.6806	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5736	Approved
0.6774	Remote Similarity	NPD1693	Approved
0.6769	Remote Similarity	NPD5697	Approved
0.6746	Remote Similarity	NPD9495	Approved
0.6744	Remote Similarity	NPD1237	Approved
0.6742	Remote Similarity	NPD6883	Approved
0.6742	Remote Similarity	NPD7102	Approved
0.6742	Remote Similarity	NPD7290	Approved
0.6736	Remote Similarity	NPD7055	Discontinued
0.6735	Remote Similarity	NPD6355	Discontinued
0.6721	Remote Similarity	NPD5785	Approved
0.6718	Remote Similarity	NPD6406	Approved
0.6692	Remote Similarity	NPD6847	Approved
0.6692	Remote Similarity	NPD6675	Approved
0.6692	Remote Similarity	NPD7128	Approved
0.6692	Remote Similarity	NPD6402	Approved
0.6692	Remote Similarity	NPD6617	Approved
0.6692	Remote Similarity	NPD6869	Approved
0.6692	Remote Similarity	NPD8130	Phase 1
0.6692	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD1930	Approved
0.6667	Remote Similarity	NPD2650	Approved
0.6667	Remote Similarity	NPD1929	Approved
0.6667	Remote Similarity	NPD6190	Approved
0.6667	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD2652	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6637	Approved
0.6667	Remote Similarity	NPD7009	Phase 2
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6642	Remote Similarity	NPD8297	Approved
0.6642	Remote Similarity	NPD6882	Approved
0.6617	Remote Similarity	NPD6371	Approved
0.6615	Remote Similarity	NPD164	Approved
0.6613	Remote Similarity	NPD1088	Approved
0.6603	Remote Similarity	NPD6273	Approved
0.6601	Remote Similarity	NPD4628	Phase 3
0.6596	Remote Similarity	NPD4806	Approved
0.6596	Remote Similarity	NPD4807	Approved
0.6594	Remote Similarity	NPD7610	Discontinued
0.6591	Remote Similarity	NPD7320	Approved
0.6591	Remote Similarity	NPD6011	Approved
0.6585	Remote Similarity	NPD3673	Approved
0.6585	Remote Similarity	NPD3672	Approved
0.6575	Remote Similarity	NPD7008	Discontinued
0.6571	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5305	Approved
0.6571	Remote Similarity	NPD5306	Approved
0.6552	Remote Similarity	NPD3661	Approved
0.6552	Remote Similarity	NPD3663	Approved
0.6552	Remote Similarity	NPD3662	Phase 3
0.6552	Remote Similarity	NPD3664	Approved
0.6535	Remote Similarity	NPD6084	Phase 2
0.6535	Remote Similarity	NPD6083	Phase 2
0.6529	Remote Similarity	NPD7685	Pre-registration
0.6529	Remote Similarity	NPD6764	Approved
0.6529	Remote Similarity	NPD6765	Approved
0.6522	Remote Similarity	NPD5760	Phase 2
0.6522	Remote Similarity	NPD5761	Phase 2
0.6515	Remote Similarity	NPD5701	Approved
0.6513	Remote Similarity	NPD5762	Approved
0.6513	Remote Similarity	NPD5763	Approved
0.6504	Remote Similarity	NPD5346	Phase 2
0.6504	Remote Similarity	NPD5347	Phase 2
0.6496	Remote Similarity	NPD4766	Approved
0.6496	Remote Similarity	NPD5951	Approved
0.6494	Remote Similarity	NPD8166	Discontinued
0.6479	Remote Similarity	NPD6287	Discontinued
0.6462	Remote Similarity	NPD5211	Phase 2
0.6462	Remote Similarity	NPD1932	Approved
0.6452	Remote Similarity	NPD1089	Approved
0.6452	Remote Similarity	NPD1090	Approved
0.6452	Remote Similarity	NPD1086	Approved
0.6449	Remote Similarity	NPD7115	Discovery
0.6438	Remote Similarity	NPD7084	Phase 3
0.6437	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD7798	Approved
0.6433	Remote Similarity	NPD8368	Discontinued
0.6433	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD9545	Approved
0.6419	Remote Similarity	NPD3268	Approved
0.6418	Remote Similarity	NPD2329	Discontinued
0.6416	Remote Similarity	NPD8407	Phase 2
0.6408	Remote Similarity	NPD4136	Approved
0.6408	Remote Similarity	NPD4106	Approved
0.6408	Remote Similarity	NPD4135	Approved
0.6405	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD969	Suspended
0.6395	Remote Similarity	NPD7962	Phase 2
0.6382	Remote Similarity	NPD7033	Discontinued
0.6379	Remote Similarity	NPD6785	Approved
0.6379	Remote Similarity	NPD6784	Approved
0.6378	Remote Similarity	NPD5695	Phase 3
0.6378	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD7715	Approved
0.6376	Remote Similarity	NPD7714	Approved
0.6371	Remote Similarity	NPD800	Approved
0.637	Remote Similarity	NPD1317	Discontinued
0.6364	Remote Similarity	NPD5141	Approved
0.6357	Remote Similarity	NPD7101	Approved
0.6357	Remote Similarity	NPD5696	Approved
0.6357	Remote Similarity	NPD7100	Approved
0.6352	Remote Similarity	NPD7606	Phase 3
0.6343	Remote Similarity	NPD8434	Phase 2
0.6341	Remote Similarity	NPD4793	Discontinued
0.6333	Remote Similarity	NPD6435	Approved
0.6333	Remote Similarity	NPD4140	Approved
0.6328	Remote Similarity	NPD1989	Approved
0.6327	Remote Similarity	NPD5204	Approved
0.6324	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5363	Approved
0.6309	Remote Similarity	NPD3764	Approved
0.6308	Remote Similarity	NPD5286	Approved
0.6308	Remote Similarity	NPD4696	Approved
0.6308	Remote Similarity	NPD1238	Approved
0.6308	Remote Similarity	NPD5285	Approved
0.6301	Remote Similarity	NPD2797	Approved
0.6299	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD7604	Phase 2
0.6287	Remote Similarity	NPD8127	Discontinued
0.6286	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6335	Approved
0.6286	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD2575	Approved
0.6282	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6053	Discontinued
0.6273	Remote Similarity	NPD7458	Discontinued
0.6268	Remote Similarity	NPD4102	Approved
0.6268	Remote Similarity	NPD5585	Approved
0.6268	Remote Similarity	NPD4105	Approved
0.6267	Remote Similarity	NPD6233	Phase 2
0.626	Remote Similarity	NPD5786	Approved
0.6259	Remote Similarity	NPD6274	Approved
0.625	Remote Similarity	NPD226	Approved
0.625	Remote Similarity	NPD6049	Phase 2
0.625	Remote Similarity	NPD2609	Approved
0.625	Remote Similarity	NPD3132	Approved
0.625	Remote Similarity	NPD4215	Approved
0.625	Remote Similarity	NPD4218	Approved
0.625	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4233	Approved
0.625	Remote Similarity	NPD4216	Approved
0.625	Remote Similarity	NPD2610	Approved
0.625	Remote Similarity	NPD2612	Approved
0.625	Remote Similarity	NPD2608	Approved
0.625	Remote Similarity	NPD3131	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