NPASS Compound

Structure

NPC54844 OpenBabel07101718232D 36 37 0 0 0 0 0 0 0 0999 V2000 2.5981 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 21 27 2 0 0 0 0 21 29 1 0 0 0 0 22 27 1 0 0 0 0 22 30 2 0 0 0 0 23 28 2 0 0 0 0 23 31 1 0 0 0 0 24 28 1 0 0 0 0 24 32 2 0 0 0 0 25 29 2 0 0 0 0 25 30 1 0 0 0 0 26 31 2 0 0 0 0 26 32 1 0 0 0 0 29 33 1 0 0 0 0 30 34 1 0 0 0 0 31 35 1 0 0 0 0 32 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.36
Volume:	561.621
LogP:	8.751
LogD:	5.037
LogS:	-2.009
# Rotatable Bonds:	20
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.109
Synthetic Accessibility Score:	2.381
Fsp3:	0.562
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.293
MDCK Permeability:	1.4220036064216401e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	100.7134017944336%
Volume Distribution (VD):	3.746
Pgp-substrate:	0.346674382686615%

ADMET: Metabolism

CYP1A2-inhibitor:	0.416
CYP1A2-substrate:	0.167
CYP2C19-inhibitor:	0.823
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.134
CYP2C9-substrate:	0.997
CYP2D6-inhibitor:	0.974
CYP2D6-substrate:	0.793
CYP3A4-inhibitor:	0.622
CYP3A4-substrate:	0.047

ADMET: Excretion

Clearance (CL):	6.549
Half-life (T1/2):	0.899

ADMET: Toxicity

hERG Blockers:	0.486
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.009
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.987
Carcinogencity:	0.015
Eye Corrosion:	0.432
Eye Irritation:	0.954
Respiratory Toxicity:	0.646

Download Data

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

Natural Product: NPC54844

Natural Product ID:	NPC54844
*Common Name:**	Oncostemonol G
IUPAC Name:	5-[(Z)-20-(3,5-dihydroxyphenyl)icos-10-enyl]benzene-1,3-diol
Synonyms:	oncostemonol G
Standard InCHIKey:	VCUZIGUMUKBBSU-UPHRSURJSA-N
Standard InCHI:	InChI=1S/C32H48O4/c33-29-21-27(22-30(34)25-29)19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20-28-23-31(35)26-32(36)24-28/h1-2,21-26,33-36H,3-20H2/b2-1-
SMILES:	Oc1cc(CCCCCCCCC/C=CCCCCCCCCCc2cc(O)cc(c2)O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465258
PubChem CID:	10345751
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

*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
NPO33313	oncostemon bojerianum	Species	n.a.	n.a.	leaves	Madagascar rainforest	n.a.	PMID[12444688]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	10.2	ug.mL-1	PMID[475406]

☑ 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 NPC54844 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	304
0.1-0.2	1532
0.2-0.3	4514
0.3-0.4	14152
0.4-0.5	5097
0.5-0.6	8179
0.6-0.7	6794
0.7-0.8	1794
0.8-0.85	190
0.85-0.9	73
0.9-0.95	54
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9899	High Similarity	NPC302681
0.9899	High Similarity	NPC39097
0.9899	High Similarity	NPC39664
0.9899	High Similarity	NPC109691
0.9899	High Similarity	NPC118286
0.9899	High Similarity	NPC470700
0.9798	High Similarity	NPC246056
0.9798	High Similarity	NPC134829
0.9697	High Similarity	NPC241891
0.9495	High Similarity	NPC100340
0.9495	High Similarity	NPC143659
0.9495	High Similarity	NPC284011
0.9495	High Similarity	NPC72947
0.94	High Similarity	NPC106396
0.94	High Similarity	NPC146798
0.94	High Similarity	NPC85479
0.94	High Similarity	NPC249828
0.94	High Similarity	NPC24404
0.94	High Similarity	NPC222522
0.94	High Similarity	NPC94351
0.94	High Similarity	NPC302219
0.94	High Similarity	NPC71002
0.94	High Similarity	NPC168303
0.94	High Similarity	NPC313030
0.94	High Similarity	NPC53051
0.94	High Similarity	NPC242342
0.9394	High Similarity	NPC10588
0.9307	High Similarity	NPC30506
0.9307	High Similarity	NPC102216
0.93	High Similarity	NPC294186
0.93	High Similarity	NPC24407
0.93	High Similarity	NPC192032
0.93	High Similarity	NPC11280
0.93	High Similarity	NPC137415
0.93	High Similarity	NPC147310
0.93	High Similarity	NPC166313
0.9245	High Similarity	NPC23804
0.9231	High Similarity	NPC33728
0.9231	High Similarity	NPC19808
0.92	High Similarity	NPC166761
0.9192	High Similarity	NPC291789
0.9151	High Similarity	NPC166995
0.9151	High Similarity	NPC43525
0.9135	High Similarity	NPC174981
0.9065	High Similarity	NPC261343
0.9057	High Similarity	NPC224527
0.9057	High Similarity	NPC225679
0.9057	High Similarity	NPC165770
0.9057	High Similarity	NPC4493
0.9057	High Similarity	NPC476632
0.9038	High Similarity	NPC204901
0.9038	High Similarity	NPC158253
0.9038	High Similarity	NPC61033
0.9038	High Similarity	NPC232523
0.9038	High Similarity	NPC305603
0.9029	High Similarity	NPC292452
0.9029	High Similarity	NPC474839
0.901	High Similarity	NPC248573
0.901	High Similarity	NPC161571
0.901	High Similarity	NPC275053
0.899	High Similarity	NPC32714
0.8942	High Similarity	NPC12640
0.8942	High Similarity	NPC201662
0.8942	High Similarity	NPC99836
0.8932	High Similarity	NPC119860
0.8909	High Similarity	NPC127894
0.8909	High Similarity	NPC15860
0.8909	High Similarity	NPC219070
0.8909	High Similarity	NPC470760
0.8909	High Similarity	NPC470759
0.8889	High Similarity	NPC76938
0.8889	High Similarity	NPC117846
0.8879	High Similarity	NPC268032
0.8846	High Similarity	NPC37802
0.8829	High Similarity	NPC9592
0.8829	High Similarity	NPC48781
0.8818	High Similarity	NPC115808
0.8818	High Similarity	NPC114064
0.8807	High Similarity	NPC107240
0.8785	High Similarity	NPC475018
0.8774	High Similarity	NPC63698
0.8774	High Similarity	NPC61885
0.8762	High Similarity	NPC248904
0.875	High Similarity	NPC218879
0.875	High Similarity	NPC244513
0.875	High Similarity	NPC227458
0.8727	High Similarity	NPC246760
0.8727	High Similarity	NPC53906
0.8727	High Similarity	NPC84999
0.8692	High Similarity	NPC186385
0.8692	High Similarity	NPC299568
0.8692	High Similarity	NPC202647
0.8661	High Similarity	NPC144343
0.8641	High Similarity	NPC294741
0.8636	High Similarity	NPC22610
0.8636	High Similarity	NPC276737
0.8614	High Similarity	NPC274678
0.86	High Similarity	NPC306884
0.86	High Similarity	NPC147284
0.86	High Similarity	NPC94139
0.86	High Similarity	NPC162314
0.86	High Similarity	NPC3358
0.86	High Similarity	NPC295295
0.86	High Similarity	NPC210497
0.8598	High Similarity	NPC34864
0.8598	High Similarity	NPC105727
0.8598	High Similarity	NPC114392
0.8598	High Similarity	NPC58427
0.8596	High Similarity	NPC24125
0.8586	High Similarity	NPC192
0.8584	High Similarity	NPC217174
0.8571	High Similarity	NPC69261
0.8571	High Similarity	NPC323810
0.8571	High Similarity	NPC33270
0.8571	High Similarity	NPC474933
0.8571	High Similarity	NPC277588
0.8559	High Similarity	NPC808
0.8522	High Similarity	NPC237667
0.8515	High Similarity	NPC151715
0.8509	High Similarity	NPC69006
0.8509	High Similarity	NPC223451
0.8505	High Similarity	NPC176527
0.8496	Intermediate Similarity	NPC190514
0.8482	Intermediate Similarity	NPC123559
0.8482	Intermediate Similarity	NPC141090
0.8482	Intermediate Similarity	NPC150624
0.8476	Intermediate Similarity	NPC168393
0.8476	Intermediate Similarity	NPC315022
0.8448	Intermediate Similarity	NPC122175
0.8431	Intermediate Similarity	NPC26244
0.8421	Intermediate Similarity	NPC184302
0.8421	Intermediate Similarity	NPC191866
0.8396	Intermediate Similarity	NPC315936
0.8393	Intermediate Similarity	NPC472893
0.8393	Intermediate Similarity	NPC167934
0.839	Intermediate Similarity	NPC249836
0.8381	Intermediate Similarity	NPC7686
0.8381	Intermediate Similarity	NPC40258
0.8381	Intermediate Similarity	NPC91461
0.8378	Intermediate Similarity	NPC162113
0.8378	Intermediate Similarity	NPC62546
0.8378	Intermediate Similarity	NPC263753
0.8378	Intermediate Similarity	NPC319803
0.8376	Intermediate Similarity	NPC53567
0.8365	Intermediate Similarity	NPC80027
0.8362	Intermediate Similarity	NPC39029
0.8362	Intermediate Similarity	NPC476633
0.835	Intermediate Similarity	NPC132271
0.835	Intermediate Similarity	NPC473388
0.835	Intermediate Similarity	NPC292730
0.835	Intermediate Similarity	NPC82664
0.835	Intermediate Similarity	NPC216520
0.8333	Intermediate Similarity	NPC206
0.8317	Intermediate Similarity	NPC45040
0.8305	Intermediate Similarity	NPC174729
0.8305	Intermediate Similarity	NPC139774
0.8305	Intermediate Similarity	NPC140521
0.8305	Intermediate Similarity	NPC78446
0.8304	Intermediate Similarity	NPC180508
0.8304	Intermediate Similarity	NPC228287
0.8291	Intermediate Similarity	NPC120172
0.8291	Intermediate Similarity	NPC77789
0.8291	Intermediate Similarity	NPC18128
0.8286	Intermediate Similarity	NPC12931
0.8286	Intermediate Similarity	NPC70677
0.8286	Intermediate Similarity	NPC48730
0.8286	Intermediate Similarity	NPC248396
0.8286	Intermediate Similarity	NPC213730
0.8286	Intermediate Similarity	NPC129373
0.8286	Intermediate Similarity	NPC130756
0.8273	Intermediate Similarity	NPC94045
0.8273	Intermediate Similarity	NPC2682
0.8273	Intermediate Similarity	NPC168657
0.8273	Intermediate Similarity	NPC242178
0.8246	Intermediate Similarity	NPC195466
0.8246	Intermediate Similarity	NPC50521
0.8246	Intermediate Similarity	NPC221549
0.8246	Intermediate Similarity	NPC244816
0.8241	Intermediate Similarity	NPC67250
0.823	Intermediate Similarity	NPC232165
0.8224	Intermediate Similarity	NPC471511
0.822	Intermediate Similarity	NPC233526
0.822	Intermediate Similarity	NPC136319
0.822	Intermediate Similarity	NPC282496
0.8208	Intermediate Similarity	NPC12221
0.82	Intermediate Similarity	NPC27974
0.8198	Intermediate Similarity	NPC296920
0.8198	Intermediate Similarity	NPC187583
0.8198	Intermediate Similarity	NPC257430
0.8198	Intermediate Similarity	NPC179002
0.8198	Intermediate Similarity	NPC90520
0.819	Intermediate Similarity	NPC51333
0.819	Intermediate Similarity	NPC92730
0.819	Intermediate Similarity	NPC132078
0.819	Intermediate Similarity	NPC472071
0.819	Intermediate Similarity	NPC78119
0.819	Intermediate Similarity	NPC216468
0.819	Intermediate Similarity	NPC260775
0.8182	Intermediate Similarity	NPC228343
0.8182	Intermediate Similarity	NPC254833

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 NPC54844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	962
0.2-0.3	1340
0.3-0.4	2937
0.4-0.5	1958
0.5-0.6	1178
0.6-0.7	435
0.7-0.8	48
0.8-0.85	8
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.901	High Similarity	NPD1242	Phase 1
0.8692	High Similarity	NPD4750	Phase 3
0.8558	High Similarity	NPD940	Approved
0.8558	High Similarity	NPD846	Approved
0.8431	Intermediate Similarity	NPD2860	Approved
0.8431	Intermediate Similarity	NPD2859	Approved
0.8365	Intermediate Similarity	NPD3020	Approved
0.8333	Intermediate Similarity	NPD2934	Approved
0.8333	Intermediate Similarity	NPD2933	Approved
0.8182	Intermediate Similarity	NPD3021	Approved
0.8182	Intermediate Similarity	NPD3022	Approved
0.8077	Intermediate Similarity	NPD844	Approved
0.783	Intermediate Similarity	NPD288	Approved
0.7823	Intermediate Similarity	NPD3027	Phase 3
0.781	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD7635	Approved
0.7778	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD4625	Phase 3
0.7679	Intermediate Similarity	NPD2342	Discontinued
0.7677	Intermediate Similarity	NPD9089	Approved
0.7623	Intermediate Similarity	NPD4749	Approved
0.7603	Intermediate Similarity	NPD1610	Phase 2
0.76	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4908	Phase 1
0.7576	Intermediate Similarity	NPD9093	Approved
0.7563	Intermediate Similarity	NPD1548	Phase 1
0.7547	Intermediate Similarity	NPD845	Approved
0.7544	Intermediate Similarity	NPD1792	Phase 2
0.752	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6671	Approved
0.7455	Intermediate Similarity	NPD3028	Approved
0.7451	Intermediate Similarity	NPD111	Approved
0.744	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1445	Approved
0.7434	Intermediate Similarity	NPD1444	Approved
0.7385	Intermediate Similarity	NPD2568	Approved
0.7364	Intermediate Similarity	NPD943	Approved
0.7364	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD1613	Approved
0.736	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD2234	Approved
0.7288	Intermediate Similarity	NPD2229	Approved
0.7288	Intermediate Similarity	NPD2228	Approved
0.7273	Intermediate Similarity	NPD3091	Approved
0.7248	Intermediate Similarity	NPD1809	Phase 2
0.7238	Intermediate Similarity	NPD9094	Approved
0.7227	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3094	Phase 2
0.7213	Intermediate Similarity	NPD4093	Discontinued
0.72	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2983	Phase 2
0.72	Intermediate Similarity	NPD2982	Phase 2
0.7177	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD3092	Approved
0.7177	Intermediate Similarity	NPD1201	Approved
0.7154	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD3019	Approved
0.7154	Intermediate Similarity	NPD2286	Discontinued
0.7154	Intermediate Similarity	NPD6405	Approved
0.7154	Intermediate Similarity	NPD6407	Approved
0.7154	Intermediate Similarity	NPD4059	Approved
0.7154	Intermediate Similarity	NPD2932	Approved
0.7143	Intermediate Similarity	NPD5283	Phase 1
0.713	Intermediate Similarity	NPD968	Approved
0.712	Intermediate Similarity	NPD2981	Phase 2
0.7117	Intermediate Similarity	NPD9273	Approved
0.7109	Intermediate Similarity	NPD3018	Phase 2
0.7109	Intermediate Similarity	NPD2861	Phase 2
0.7107	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6100	Approved
0.709	Intermediate Similarity	NPD6099	Approved
0.7087	Intermediate Similarity	NPD1470	Approved
0.7077	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD422	Phase 1
0.7034	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD602	Approved
0.7031	Intermediate Similarity	NPD858	Approved
0.7031	Intermediate Similarity	NPD859	Approved
0.7031	Intermediate Similarity	NPD599	Approved
0.7018	Intermediate Similarity	NPD9500	Approved
0.7016	Intermediate Similarity	NPD3095	Discontinued
0.7015	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD5310	Approved
0.7008	Intermediate Similarity	NPD5311	Approved
0.6992	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD228	Approved
0.6949	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD497	Approved
0.6942	Remote Similarity	NPD1793	Approved
0.6942	Remote Similarity	NPD1791	Approved
0.6929	Remote Similarity	NPD4659	Approved
0.6917	Remote Similarity	NPD9379	Approved
0.6917	Remote Similarity	NPD7843	Approved
0.6917	Remote Similarity	NPD9377	Approved
0.6899	Remote Similarity	NPD6584	Phase 3
0.6889	Remote Similarity	NPD1510	Phase 2
0.6884	Remote Similarity	NPD3892	Phase 2
0.6884	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.688	Remote Similarity	NPD1751	Approved
0.688	Remote Similarity	NPD4589	Approved
0.6869	Remote Similarity	NPD9087	Approved
0.6866	Remote Similarity	NPD5314	Approved
0.686	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.686	Remote Similarity	NPD498	Approved
0.686	Remote Similarity	NPD495	Approved
0.686	Remote Similarity	NPD496	Approved
0.6857	Remote Similarity	NPD7390	Discontinued
0.6855	Remote Similarity	NPD7741	Discontinued
0.6855	Remote Similarity	NPD5303	Approved
0.6855	Remote Similarity	NPD7330	Discontinued
0.6855	Remote Similarity	NPD5304	Approved
0.685	Remote Similarity	NPD9269	Phase 2
0.685	Remote Similarity	NPD2230	Approved
0.685	Remote Similarity	NPD2562	Approved
0.685	Remote Similarity	NPD1608	Approved
0.685	Remote Similarity	NPD2233	Approved
0.685	Remote Similarity	NPD2232	Approved
0.685	Remote Similarity	NPD2561	Approved
0.6846	Remote Similarity	NPD5736	Approved
0.6842	Remote Similarity	NPD1240	Approved
0.6842	Remote Similarity	NPD3062	Approved
0.6842	Remote Similarity	NPD3059	Approved
0.6842	Remote Similarity	NPD3061	Approved
0.6842	Remote Similarity	NPD6346	Approved
0.6842	Remote Similarity	NPD1555	Discontinued
0.6842	Remote Similarity	NPD2238	Phase 2
0.6838	Remote Similarity	NPD5405	Approved
0.6838	Remote Similarity	NPD5404	Approved
0.6838	Remote Similarity	NPD5406	Approved
0.6838	Remote Similarity	NPD5408	Approved
0.6825	Remote Similarity	NPD1981	Approved
0.6825	Remote Similarity	NPD1983	Approved
0.6825	Remote Similarity	NPD1980	Approved
0.6822	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3055	Approved
0.6822	Remote Similarity	NPD4103	Phase 2
0.6822	Remote Similarity	NPD3053	Approved
0.681	Remote Similarity	NPD9610	Approved
0.681	Remote Similarity	NPD9608	Approved
0.6809	Remote Similarity	NPD7447	Phase 1
0.6807	Remote Similarity	NPD5451	Approved
0.6803	Remote Similarity	NPD9614	Approved
0.6803	Remote Similarity	NPD9618	Approved
0.68	Remote Similarity	NPD9268	Approved
0.6797	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7266	Discontinued
0.6777	Remote Similarity	NPD5535	Approved
0.6765	Remote Similarity	NPD9088	Approved
0.6763	Remote Similarity	NPD3750	Approved
0.6748	Remote Similarity	NPD709	Approved
0.6748	Remote Similarity	NPD7157	Approved
0.6746	Remote Similarity	NPD9381	Approved
0.6746	Remote Similarity	NPD9384	Approved
0.6744	Remote Similarity	NPD6696	Suspended
0.6742	Remote Similarity	NPD7095	Approved
0.6741	Remote Similarity	NPD1607	Approved
0.6724	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD2684	Approved
0.672	Remote Similarity	NPD1759	Phase 1
0.6719	Remote Similarity	NPD2235	Phase 2
0.6719	Remote Similarity	NPD2231	Phase 2
0.6716	Remote Similarity	NPD4060	Phase 1
0.6715	Remote Similarity	NPD2935	Discontinued
0.6694	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD3847	Discontinued
0.6693	Remote Similarity	NPD3026	Approved
0.6693	Remote Similarity	NPD3023	Approved
0.6692	Remote Similarity	NPD1164	Approved
0.6692	Remote Similarity	NPD2797	Approved
0.6692	Remote Similarity	NPD3764	Approved
0.6692	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3025	Approved
0.6667	Remote Similarity	NPD6582	Phase 2
0.6667	Remote Similarity	NPD3024	Approved
0.6667	Remote Similarity	NPD6583	Phase 3
0.6667	Remote Similarity	NPD1755	Approved
0.6667	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9294	Approved
0.6667	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD6663	Approved
0.6642	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD7451	Discontinued
0.6641	Remote Similarity	NPD2195	Approved
0.6641	Remote Similarity	NPD2194	Approved
0.6641	Remote Similarity	NPD1091	Approved
0.664	Remote Similarity	NPD9613	Approved
0.664	Remote Similarity	NPD16	Approved
0.664	Remote Similarity	NPD856	Approved
0.664	Remote Similarity	NPD1758	Phase 1
0.664	Remote Similarity	NPD9616	Approved
0.664	Remote Similarity	NPD9615	Approved
0.6639	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4818	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