NPASS Compound

Structure

NPC107963 OpenBabel07101718322D 23 26 0 0 1 0 0 0 0 0999 V2000 -1.7796 -1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2796 2.9593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7796 2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1691 0.1229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3383 -1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -0.9067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7796 1.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1473 -0.0850 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7796 2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 0.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8904 0.5841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2518 -1.0796 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 14 1 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 12 16 1 0 0 0 0 12 19 1 0 0 0 0 13 19 1 0 0 0 0 13 22 1 0 0 0 0 14 20 1 6 0 0 0 15 17 1 0 0 0 0 15 18 1 1 0 0 0 16 21 1 1 0 0 0 16 22 1 0 0 0 0 18 20 1 6 0 0 0 19 10 1 6 0 0 0 19 23 1 0 0 0 0 20 11 1 1 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.25
Volume:	346.621
LogP:	4.455
LogD:	3.931
LogS:	-4.882
# Rotatable Bonds:	0
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.723
Synthetic Accessibility Score:	5.379
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.7
MDCK Permeability:	2.6174888262175955e-05
Pgp-inhibitor:	0.079
Pgp-substrate:	0.314
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.185
Plasma Protein Binding (PPB):	94.74353790283203%
Volume Distribution (VD):	1.684
Pgp-substrate:	5.815769672393799%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.137
CYP2C19-substrate:	0.916
CYP2C9-inhibitor:	0.306
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.81
CYP3A4-substrate:	0.581

ADMET: Excretion

Clearance (CL):	12.567
Half-life (T1/2):	0.162

ADMET: Toxicity

hERG Blockers:	0.125
Human Hepatotoxicity (H-HT):	0.688
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.111
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.824
Carcinogencity:	0.729
Eye Corrosion:	0.053
Eye Irritation:	0.329
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC107963

Natural Product ID:	NPC107963
*Common Name:**	VOHURPICLQUNQE-XSBFNCLBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VOHURPICLQUNQE-XSBFNCLBSA-N
Standard InCHI:	InChI=1S/C20H34O3/c1-14-6-7-15-17(2,3)8-5-9-18(15,4)20(14)11-10-19(23-20)12-16(21)22-13-19/h14-16,21H,5-13H2,1-4H3/t14-,15+,16+,18+,19+,20-/m1/s1
SMILES:	C[C@@H]1CC[C@H]2C(C)(C)CCC[C@]2(C)[C@]21CC[C@@]1(C[C@@H](O)OC1)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431871
PubChem CID:	72701754
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
NPO32859	leucas stelligera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24117130]

☑ 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
Others	9

Activity Type	# Activity
Cell Line	6
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	GI	=	14.43	%	PMID[566659]
NPT65	Cell Line	HepG2	Homo sapiens	GI	=	6.92	%	PMID[566659]
NPT1970	Cell Line	THP-1	Homo sapiens	GI	=	21.74	%	PMID[566659]
NPT1970	Cell Line	THP-1	Homo sapiens	GI	=	8.18	%	PMID[566659]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	42.4	%	PMID[566659]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	28.98	%	PMID[566659]
NPT19	Organism	Escherichia coli	Escherichia coli	GI	=	23.15	%	PMID[566659]
NPT1107	Organism	Mycobacterium smegmatis str. MC2 155	Mycobacterium smegmatis str. MC2 155	Inhibition	=	47.83	%	PMID[566659]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	IC90	=	14.88	ug.mL-1	PMID[566659]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	IC50	=	5.55	ug.mL-1	PMID[566659]

☑ 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 NPC107963 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	379
0.1-0.2	4103
0.2-0.3	14205
0.3-0.4	10591
0.4-0.5	5767
0.5-0.6	5419
0.6-0.7	1769
0.7-0.8	440
0.8-0.85	15
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8974	High Similarity	NPC18953
0.8684	High Similarity	NPC177343
0.8642	High Similarity	NPC62202
0.8642	High Similarity	NPC110365
0.8642	High Similarity	NPC213658
0.8642	High Similarity	NPC45833
0.8537	High Similarity	NPC470872
0.8462	Intermediate Similarity	NPC186588
0.8462	Intermediate Similarity	NPC471216
0.8462	Intermediate Similarity	NPC471217
0.8395	Intermediate Similarity	NPC235402
0.8354	Intermediate Similarity	NPC71541
0.8293	Intermediate Similarity	NPC471411
0.8293	Intermediate Similarity	NPC471410
0.8293	Intermediate Similarity	NPC268633
0.8289	Intermediate Similarity	NPC472952
0.8289	Intermediate Similarity	NPC472950
0.8214	Intermediate Similarity	NPC82955
0.8205	Intermediate Similarity	NPC272841
0.8193	Intermediate Similarity	NPC210658
0.8193	Intermediate Similarity	NPC161928
0.8171	Intermediate Similarity	NPC290612
0.8158	Intermediate Similarity	NPC308489
0.8148	Intermediate Similarity	NPC241959
0.814	Intermediate Similarity	NPC475307
0.8095	Intermediate Similarity	NPC128475
0.8072	Intermediate Similarity	NPC107603
0.8025	Intermediate Similarity	NPC2096
0.8025	Intermediate Similarity	NPC208912
0.8025	Intermediate Similarity	NPC470611
0.8023	Intermediate Similarity	NPC210759
0.8023	Intermediate Similarity	NPC307167
0.8023	Intermediate Similarity	NPC229801
0.8023	Intermediate Similarity	NPC59006
0.8	Intermediate Similarity	NPC20822
0.8	Intermediate Similarity	NPC472951
0.8	Intermediate Similarity	NPC472943
0.7976	Intermediate Similarity	NPC472396
0.7976	Intermediate Similarity	NPC140446
0.7976	Intermediate Similarity	NPC43912
0.7955	Intermediate Similarity	NPC21897
0.7931	Intermediate Similarity	NPC311246
0.7931	Intermediate Similarity	NPC167644
0.7927	Intermediate Similarity	NPC470070
0.7927	Intermediate Similarity	NPC474284
0.7927	Intermediate Similarity	NPC475820
0.7927	Intermediate Similarity	NPC213737
0.7927	Intermediate Similarity	NPC474346
0.7927	Intermediate Similarity	NPC474253
0.7922	Intermediate Similarity	NPC470151
0.7907	Intermediate Similarity	NPC473542
0.7875	Intermediate Similarity	NPC81074
0.7875	Intermediate Similarity	NPC477282
0.7857	Intermediate Similarity	NPC474008
0.7848	Intermediate Similarity	NPC474574
0.7848	Intermediate Similarity	NPC11907
0.7848	Intermediate Similarity	NPC64081
0.7848	Intermediate Similarity	NPC133596
0.7841	Intermediate Similarity	NPC113500
0.7841	Intermediate Similarity	NPC175
0.7841	Intermediate Similarity	NPC3538
0.7841	Intermediate Similarity	NPC252253
0.7841	Intermediate Similarity	NPC30687
0.7841	Intermediate Similarity	NPC477224
0.7841	Intermediate Similarity	NPC305418
0.7841	Intermediate Similarity	NPC45959
0.7831	Intermediate Similarity	NPC474156
0.7821	Intermediate Similarity	NPC270306
0.7821	Intermediate Similarity	NPC231680
0.7821	Intermediate Similarity	NPC91387
0.7816	Intermediate Similarity	NPC5632
0.7816	Intermediate Similarity	NPC149966
0.7805	Intermediate Similarity	NPC477446
0.7805	Intermediate Similarity	NPC477447
0.7805	Intermediate Similarity	NPC470155
0.7791	Intermediate Similarity	NPC131466
0.7763	Intermediate Similarity	NPC471879
0.7753	Intermediate Similarity	NPC473067
0.7753	Intermediate Similarity	NPC473065
0.7753	Intermediate Similarity	NPC473064
0.775	Intermediate Similarity	NPC477577
0.7727	Intermediate Similarity	NPC149400
0.7727	Intermediate Similarity	NPC171741
0.7727	Intermediate Similarity	NPC211845
0.7727	Intermediate Similarity	NPC323231
0.7727	Intermediate Similarity	NPC88962
0.7727	Intermediate Similarity	NPC256104
0.7727	Intermediate Similarity	NPC18724
0.7727	Intermediate Similarity	NPC182740
0.7727	Intermediate Similarity	NPC470623
0.7727	Intermediate Similarity	NPC224003
0.7727	Intermediate Similarity	NPC122083
0.7727	Intermediate Similarity	NPC144790
0.7701	Intermediate Similarity	NPC279329
0.7692	Intermediate Similarity	NPC209666
0.7692	Intermediate Similarity	NPC292775
0.7692	Intermediate Similarity	NPC200167
0.7692	Intermediate Similarity	NPC31046
0.7692	Intermediate Similarity	NPC53868
0.7692	Intermediate Similarity	NPC166250
0.7683	Intermediate Similarity	NPC470154
0.7683	Intermediate Similarity	NPC470156
0.7674	Intermediate Similarity	NPC471221
0.7674	Intermediate Similarity	NPC281004
0.7674	Intermediate Similarity	NPC221993
0.7667	Intermediate Similarity	NPC203434
0.7667	Intermediate Similarity	NPC304011
0.7667	Intermediate Similarity	NPC139271
0.7667	Intermediate Similarity	NPC475765
0.7667	Intermediate Similarity	NPC476510
0.7667	Intermediate Similarity	NPC142264
0.7667	Intermediate Similarity	NPC475785
0.7667	Intermediate Similarity	NPC238796
0.7667	Intermediate Similarity	NPC237071
0.7647	Intermediate Similarity	NPC215968
0.7647	Intermediate Similarity	NPC155531
0.764	Intermediate Similarity	NPC471373
0.764	Intermediate Similarity	NPC131693
0.764	Intermediate Similarity	NPC473774
0.764	Intermediate Similarity	NPC253611
0.764	Intermediate Similarity	NPC473851
0.764	Intermediate Similarity	NPC312678
0.764	Intermediate Similarity	NPC174024
0.764	Intermediate Similarity	NPC24960
0.764	Intermediate Similarity	NPC77717
0.764	Intermediate Similarity	NPC475436
0.764	Intermediate Similarity	NPC253268
0.764	Intermediate Similarity	NPC179859
0.764	Intermediate Similarity	NPC267238
0.764	Intermediate Similarity	NPC148593
0.764	Intermediate Similarity	NPC291547
0.7614	Intermediate Similarity	NPC475878
0.7614	Intermediate Similarity	NPC36372
0.7614	Intermediate Similarity	NPC293609
0.759	Intermediate Similarity	NPC475388
0.759	Intermediate Similarity	NPC296734
0.7586	Intermediate Similarity	NPC228059
0.7586	Intermediate Similarity	NPC473472
0.7586	Intermediate Similarity	NPC102725
0.7582	Intermediate Similarity	NPC477223
0.7582	Intermediate Similarity	NPC233649
0.7582	Intermediate Similarity	NPC470028
0.7582	Intermediate Similarity	NPC477222
0.7561	Intermediate Similarity	NPC248944
0.7561	Intermediate Similarity	NPC7479
0.7561	Intermediate Similarity	NPC257296
0.7561	Intermediate Similarity	NPC16449
0.7556	Intermediate Similarity	NPC471429
0.7556	Intermediate Similarity	NPC471424
0.7556	Intermediate Similarity	NPC106701
0.7556	Intermediate Similarity	NPC205129
0.7556	Intermediate Similarity	NPC471425
0.7556	Intermediate Similarity	NPC189575
0.7556	Intermediate Similarity	NPC474399
0.7529	Intermediate Similarity	NPC232044
0.7529	Intermediate Similarity	NPC273290
0.7528	Intermediate Similarity	NPC297348
0.7528	Intermediate Similarity	NPC249204
0.7528	Intermediate Similarity	NPC477451
0.7528	Intermediate Similarity	NPC250393
0.7528	Intermediate Similarity	NPC177834
0.7528	Intermediate Similarity	NPC141769
0.7528	Intermediate Similarity	NPC234352
0.7528	Intermediate Similarity	NPC325828
0.7528	Intermediate Similarity	NPC477547
0.7528	Intermediate Similarity	NPC277774
0.7528	Intermediate Similarity	NPC48339
0.7527	Intermediate Similarity	NPC477225
0.75	Intermediate Similarity	NPC136424
0.75	Intermediate Similarity	NPC477285
0.75	Intermediate Similarity	NPC216260
0.75	Intermediate Similarity	NPC474249
0.75	Intermediate Similarity	NPC473638
0.75	Intermediate Similarity	NPC5358
0.75	Intermediate Similarity	NPC261990
0.75	Intermediate Similarity	NPC111582
0.75	Intermediate Similarity	NPC223143
0.75	Intermediate Similarity	NPC65550
0.7473	Intermediate Similarity	NPC121453
0.7471	Intermediate Similarity	NPC476435
0.7465	Intermediate Similarity	NPC132998
0.7444	Intermediate Similarity	NPC191915
0.7444	Intermediate Similarity	NPC473503
0.7444	Intermediate Similarity	NPC222731
0.7444	Intermediate Similarity	NPC291203
0.7444	Intermediate Similarity	NPC471464
0.7444	Intermediate Similarity	NPC309866
0.7444	Intermediate Similarity	NPC264101
0.7444	Intermediate Similarity	NPC294686
0.7444	Intermediate Similarity	NPC151214
0.7444	Intermediate Similarity	NPC217205
0.7442	Intermediate Similarity	NPC471240
0.7442	Intermediate Similarity	NPC477283
0.7436	Intermediate Similarity	NPC1340
0.7436	Intermediate Similarity	NPC187471
0.7436	Intermediate Similarity	NPC252182
0.7436	Intermediate Similarity	NPC470071
0.7419	Intermediate Similarity	NPC324598
0.7419	Intermediate Similarity	NPC470030
0.7416	Intermediate Similarity	NPC204881

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 NPC107963 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	407
0.1-0.2	4281
0.2-0.3	3143
0.3-0.4	718
0.4-0.5	319
0.5-0.6	235
0.6-0.7	45
0.7-0.8	2
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
0.7692	Intermediate Similarity	NPD1810	Approved
0.7692	Intermediate Similarity	NPD1811	Approved
0.7561	Intermediate Similarity	NPD6928	Phase 2
0.7528	Intermediate Similarity	NPD8171	Discontinued
0.7308	Intermediate Similarity	NPD2687	Approved
0.7308	Intermediate Similarity	NPD2254	Approved
0.7308	Intermediate Similarity	NPD2686	Approved
0.6974	Remote Similarity	NPD371	Approved
0.6962	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3669	Approved
0.6897	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD2267	Suspended
0.6322	Remote Similarity	NPD6697	Approved
0.6322	Remote Similarity	NPD6115	Approved
0.6322	Remote Similarity	NPD6118	Approved
0.6322	Remote Similarity	NPD6114	Approved
0.6292	Remote Similarity	NPD1779	Approved
0.6292	Remote Similarity	NPD1780	Approved
0.6289	Remote Similarity	NPD7991	Discontinued
0.6265	Remote Similarity	NPD4787	Phase 1
0.6207	Remote Similarity	NPD6116	Phase 1
0.619	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7327	Approved
0.6182	Remote Similarity	NPD7328	Approved
0.6163	Remote Similarity	NPD3703	Phase 2
0.6154	Remote Similarity	NPD6412	Phase 2
0.6126	Remote Similarity	NPD7516	Approved
0.6111	Remote Similarity	NPD8133	Approved
0.6106	Remote Similarity	NPD6370	Approved
0.6092	Remote Similarity	NPD6117	Approved
0.6071	Remote Similarity	NPD8294	Approved
0.6071	Remote Similarity	NPD8377	Approved
0.6049	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD8296	Approved
0.6018	Remote Similarity	NPD8335	Approved
0.6018	Remote Similarity	NPD8379	Approved
0.6018	Remote Similarity	NPD8380	Approved
0.6018	Remote Similarity	NPD8378	Approved
0.6018	Remote Similarity	NPD8033	Approved
0.6	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7525	Registered
0.6	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.598	Remote Similarity	NPD1700	Approved
0.5977	Remote Similarity	NPD3702	Approved
0.5952	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD6686	Approved
0.5929	Remote Similarity	NPD6054	Approved
0.5929	Remote Similarity	NPD6059	Approved
0.5915	Remote Similarity	NPD385	Approved
0.5915	Remote Similarity	NPD384	Approved
0.5914	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD8293	Discontinued
0.5895	Remote Similarity	NPD7524	Approved
0.5889	Remote Similarity	NPD7645	Phase 2
0.5882	Remote Similarity	NPD4244	Approved
0.5882	Remote Similarity	NPD4789	Approved
0.5882	Remote Similarity	NPD4245	Approved
0.5877	Remote Similarity	NPD7503	Approved
0.5856	Remote Similarity	NPD6940	Discontinued
0.5847	Remote Similarity	NPD7736	Approved
0.5833	Remote Similarity	NPD6705	Phase 1
0.5833	Remote Similarity	NPD5360	Phase 3
0.5833	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD7507	Approved
0.5806	Remote Similarity	NPD6695	Phase 3
0.5804	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6067	Discontinued
0.5775	Remote Similarity	NPD386	Approved
0.5775	Remote Similarity	NPD388	Approved
0.5765	Remote Similarity	NPD3698	Phase 2
0.575	Remote Similarity	NPD1145	Discontinued
0.5741	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD6015	Approved
0.5739	Remote Similarity	NPD6016	Approved
0.5726	Remote Similarity	NPD7492	Approved
0.569	Remote Similarity	NPD5988	Approved
0.5678	Remote Similarity	NPD6616	Approved
0.5667	Remote Similarity	NPD7319	Approved
0.566	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.566	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5658	Remote Similarity	NPD889	Approved
0.5658	Remote Similarity	NPD895	Approved
0.5658	Remote Similarity	NPD894	Approved
0.5658	Remote Similarity	NPD887	Approved
0.5652	Remote Similarity	NPD6930	Phase 2
0.5652	Remote Similarity	NPD6931	Approved
0.5648	Remote Similarity	NPD8174	Phase 2
0.5632	Remote Similarity	NPD5777	Approved
0.5631	Remote Similarity	NPD7638	Approved
0.563	Remote Similarity	NPD7078	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