NPASS Compound

Structure

NPC249836 OpenBabel07101719142D 38 39 0 0 0 0 0 0 0 0999 V2000 -15.5885 9.0000 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 -5.1962 8.0000 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 -6.0622 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 8.0000 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 -7.7942 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 8.0000 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 -9.5263 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 8.0000 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 -11.2583 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 7.5000 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 -13.8564 9.0000 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 -15.5885 8.0000 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 -12.1244 8.0000 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 -12.9904 9.5000 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 -13.8564 8.0000 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 -16.4545 7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 10.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 4 2 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 27 1 0 0 0 0 18 28 1 0 0 0 0 19 27 2 0 0 0 0 19 29 1 0 0 0 0 20 28 2 0 0 0 0 20 30 1 0 0 0 0 21 27 1 0 0 0 0 21 31 2 0 0 0 0 22 28 1 0 0 0 0 22 32 2 0 0 0 0 23 29 2 0 0 0 0 23 31 1 0 0 0 0 24 30 2 0 0 0 0 24 32 1 0 0 0 0 25 33 2 0 0 0 0 25 37 1 0 0 0 0 26 34 2 0 0 0 0 26 38 1 0 0 0 0 29 35 1 0 0 0 0 30 36 1 0 0 0 0 31 37 1 0 0 0 0 32 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	524.31
Volume:	573.928
LogP:	7.258
LogD:	4.247
LogS:	-2.394
# Rotatable Bonds:	20
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.089
Synthetic Accessibility Score:	2.739
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.129
MDCK Permeability:	2.6731651814770885e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.351
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	100.11737823486328%
Volume Distribution (VD):	0.882
Pgp-substrate:	0.504564106464386%

ADMET: Metabolism

CYP1A2-inhibitor:	0.336
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.771
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.182
CYP2C9-substrate:	0.991
CYP2D6-inhibitor:	0.911
CYP2D6-substrate:	0.604
CYP3A4-inhibitor:	0.653
CYP3A4-substrate:	0.071

ADMET: Excretion

Clearance (CL):	3.159
Half-life (T1/2):	0.899

ADMET: Toxicity

hERG Blockers:	0.176
Human Hepatotoxicity (H-HT):	0.015
Drug-inuced Liver Injury (DILI):	0.072
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.981
Carcinogencity:	0.028
Eye Corrosion:	0.013
Eye Irritation:	0.871
Respiratory Toxicity:	0.738

Download Data

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

Natural Product: NPC249836

Natural Product ID:	NPC249836
*Common Name:**	Oncostemonol A
IUPAC Name:	[3-[(Z)-16-(3-acetyloxy-5-hydroxyphenyl)hexadec-8-enyl]-5-hydroxyphenyl] acetate
Synonyms:
Standard InCHIKey:	KKAFTGMKZVJNPP-ARJAWSKDSA-N
Standard InCHI:	InChI=1S/C32H44O6/c1-25(33)37-31-21-27(19-29(35)23-31)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-28-20-30(36)24-32(22-28)38-26(2)34/h3-4,19-24,35-36H,5-18H2,1-2H3/b4-3-
SMILES:	CC(=O)Oc1cc(CCCCCCC/C=CCCCCCCCc2cc(O)cc(c2)OC(=O)C)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458521
PubChem CID:	643740
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002319] Phenol esters

*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	=	9.4	ug.mL-1	PMID[490286]

☑ 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 NPC249836 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	272
0.1-0.2	1450
0.2-0.3	4144
0.3-0.4	11736
0.4-0.5	6751
0.5-0.6	4414
0.6-0.7	8454
0.7-0.8	4990
0.8-0.85	430
0.85-0.9	43
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9915	High Similarity	NPC78446
0.9915	High Similarity	NPC140521
0.9237	High Similarity	NPC471498
0.9237	High Similarity	NPC471503
0.9076	High Similarity	NPC470759
0.9076	High Similarity	NPC219070
0.9076	High Similarity	NPC15860
0.9076	High Similarity	NPC127894
0.9008	High Similarity	NPC473290
0.9008	High Similarity	NPC471504
0.8992	High Similarity	NPC114064
0.8908	High Similarity	NPC53906
0.8828	High Similarity	NPC32463
0.8824	High Similarity	NPC276737
0.8824	High Similarity	NPC22610
0.876	High Similarity	NPC33270
0.876	High Similarity	NPC142530
0.876	High Similarity	NPC474933
0.876	High Similarity	NPC69261
0.873	High Similarity	NPC168259
0.8729	High Similarity	NPC255068
0.8702	High Similarity	NPC131950
0.8692	High Similarity	NPC474635
0.8692	High Similarity	NPC245120
0.8678	High Similarity	NPC150624
0.8678	High Similarity	NPC123559
0.8678	High Similarity	NPC141090
0.8647	High Similarity	NPC476171
0.8647	High Similarity	NPC474886
0.8629	High Similarity	NPC218753
0.8626	High Similarity	NPC474810
0.8618	High Similarity	NPC184302
0.8595	High Similarity	NPC808
0.8595	High Similarity	NPC167934
0.8594	High Similarity	NPC243688
0.8594	High Similarity	NPC470699
0.8571	High Similarity	NPC471719
0.8561	High Similarity	NPC309744
0.8561	High Similarity	NPC111635
0.856	High Similarity	NPC52247
0.856	High Similarity	NPC187868
0.856	High Similarity	NPC476633
0.8537	High Similarity	NPC190514
0.8516	High Similarity	NPC181361
0.8512	High Similarity	NPC228287
0.8512	High Similarity	NPC180508
0.8496	Intermediate Similarity	NPC252095
0.8492	Intermediate Similarity	NPC77789
0.8492	Intermediate Similarity	NPC18128
0.8487	Intermediate Similarity	NPC168657
0.8487	Intermediate Similarity	NPC94045
0.8487	Intermediate Similarity	NPC2682
0.8473	Intermediate Similarity	NPC472590
0.8473	Intermediate Similarity	NPC147317
0.8473	Intermediate Similarity	NPC250727
0.8473	Intermediate Similarity	NPC8899
0.8468	Intermediate Similarity	NPC85895
0.8468	Intermediate Similarity	NPC137294
0.8455	Intermediate Similarity	NPC50521
0.8455	Intermediate Similarity	NPC221549
0.8455	Intermediate Similarity	NPC244816
0.8455	Intermediate Similarity	NPC195466
0.845	Intermediate Similarity	NPC210355
0.845	Intermediate Similarity	NPC474821
0.845	Intermediate Similarity	NPC46978
0.845	Intermediate Similarity	NPC66331
0.845	Intermediate Similarity	NPC257947
0.8438	Intermediate Similarity	NPC244495
0.8438	Intermediate Similarity	NPC93219
0.8425	Intermediate Similarity	NPC136319
0.8425	Intermediate Similarity	NPC76465
0.8425	Intermediate Similarity	NPC38761
0.8425	Intermediate Similarity	NPC282496
0.8425	Intermediate Similarity	NPC315807
0.8425	Intermediate Similarity	NPC233526
0.8409	Intermediate Similarity	NPC469611
0.8409	Intermediate Similarity	NPC5423
0.8406	Intermediate Similarity	NPC471824
0.8397	Intermediate Similarity	NPC79184
0.8397	Intermediate Similarity	NPC307042
0.839	Intermediate Similarity	NPC54844
0.8385	Intermediate Similarity	NPC474651
0.8385	Intermediate Similarity	NPC474623
0.8385	Intermediate Similarity	NPC219923
0.8385	Intermediate Similarity	NPC210674
0.8385	Intermediate Similarity	NPC185066
0.8385	Intermediate Similarity	NPC474636
0.8385	Intermediate Similarity	NPC469453
0.8374	Intermediate Similarity	NPC54507
0.8374	Intermediate Similarity	NPC203113
0.8374	Intermediate Similarity	NPC229147
0.8374	Intermediate Similarity	NPC85292
0.8372	Intermediate Similarity	NPC26879
0.8372	Intermediate Similarity	NPC474632
0.8372	Intermediate Similarity	NPC230479
0.8372	Intermediate Similarity	NPC283049
0.8372	Intermediate Similarity	NPC50315
0.837	Intermediate Similarity	NPC38874
0.8359	Intermediate Similarity	NPC270030
0.8359	Intermediate Similarity	NPC228972
0.8359	Intermediate Similarity	NPC122792
0.8347	Intermediate Similarity	NPC280606
0.8346	Intermediate Similarity	NPC100099
0.8346	Intermediate Similarity	NPC302211
0.8346	Intermediate Similarity	NPC31849
0.8346	Intermediate Similarity	NPC469610
0.8346	Intermediate Similarity	NPC74137
0.8346	Intermediate Similarity	NPC36016
0.8345	Intermediate Similarity	NPC125617
0.8333	Intermediate Similarity	NPC7439
0.8333	Intermediate Similarity	NPC302107
0.8333	Intermediate Similarity	NPC91492
0.8333	Intermediate Similarity	NPC110067
0.8333	Intermediate Similarity	NPC34245
0.8333	Intermediate Similarity	NPC256555
0.8333	Intermediate Similarity	NPC102639
0.8321	Intermediate Similarity	NPC96719
0.8321	Intermediate Similarity	NPC93962
0.8321	Intermediate Similarity	NPC474289
0.8321	Intermediate Similarity	NPC16577
0.8321	Intermediate Similarity	NPC222108
0.8319	Intermediate Similarity	NPC245115
0.8308	Intermediate Similarity	NPC121740
0.8308	Intermediate Similarity	NPC258567
0.8308	Intermediate Similarity	NPC194841
0.8308	Intermediate Similarity	NPC474670
0.8308	Intermediate Similarity	NPC473221
0.8308	Intermediate Similarity	NPC224774
0.8305	Intermediate Similarity	NPC470700
0.8305	Intermediate Similarity	NPC109691
0.8305	Intermediate Similarity	NPC302681
0.8305	Intermediate Similarity	NPC39664
0.8305	Intermediate Similarity	NPC39097
0.8305	Intermediate Similarity	NPC118286
0.8295	Intermediate Similarity	NPC285040
0.8295	Intermediate Similarity	NPC208950
0.8295	Intermediate Similarity	NPC203133
0.8295	Intermediate Similarity	NPC131397
0.8295	Intermediate Similarity	NPC193544
0.8295	Intermediate Similarity	NPC475169
0.8295	Intermediate Similarity	NPC103420
0.8295	Intermediate Similarity	NPC17943
0.8295	Intermediate Similarity	NPC116907
0.8295	Intermediate Similarity	NPC117214
0.8295	Intermediate Similarity	NPC298757
0.8295	Intermediate Similarity	NPC105925
0.8295	Intermediate Similarity	NPC476254
0.8295	Intermediate Similarity	NPC472093
0.8295	Intermediate Similarity	NPC17809
0.8295	Intermediate Similarity	NPC251855
0.8295	Intermediate Similarity	NPC221077
0.8295	Intermediate Similarity	NPC233410
0.8295	Intermediate Similarity	NPC57490
0.8295	Intermediate Similarity	NPC102540
0.8295	Intermediate Similarity	NPC188022
0.8295	Intermediate Similarity	NPC113495
0.8293	Intermediate Similarity	NPC464
0.8293	Intermediate Similarity	NPC185541
0.8286	Intermediate Similarity	NPC29577
0.8286	Intermediate Similarity	NPC475896
0.8281	Intermediate Similarity	NPC96940
0.8273	Intermediate Similarity	NPC36732
0.8271	Intermediate Similarity	NPC470752
0.8271	Intermediate Similarity	NPC194277
0.8268	Intermediate Similarity	NPC75713
0.8268	Intermediate Similarity	NPC54972
0.8268	Intermediate Similarity	NPC212965
0.8264	Intermediate Similarity	NPC90520
0.8264	Intermediate Similarity	NPC296920
0.8258	Intermediate Similarity	NPC476399
0.8258	Intermediate Similarity	NPC262606
0.8258	Intermediate Similarity	NPC472338
0.8258	Intermediate Similarity	NPC474617
0.8254	Intermediate Similarity	NPC247553
0.8244	Intermediate Similarity	NPC38664
0.8244	Intermediate Similarity	NPC53986
0.8244	Intermediate Similarity	NPC274717
0.8244	Intermediate Similarity	NPC474616
0.824	Intermediate Similarity	NPC131118
0.8235	Intermediate Similarity	NPC105493
0.8235	Intermediate Similarity	NPC131198
0.8235	Intermediate Similarity	NPC35543
0.8235	Intermediate Similarity	NPC124149
0.8231	Intermediate Similarity	NPC101894
0.8231	Intermediate Similarity	NPC82299
0.8231	Intermediate Similarity	NPC276212
0.8227	Intermediate Similarity	NPC170239
0.8227	Intermediate Similarity	NPC237208
0.8227	Intermediate Similarity	NPC97937
0.8227	Intermediate Similarity	NPC275125
0.8222	Intermediate Similarity	NPC311430
0.8222	Intermediate Similarity	NPC224941
0.822	Intermediate Similarity	NPC134829
0.822	Intermediate Similarity	NPC246056
0.8217	Intermediate Similarity	NPC197351
0.8217	Intermediate Similarity	NPC106914
0.8217	Intermediate Similarity	NPC86502
0.8217	Intermediate Similarity	NPC246648
0.8217	Intermediate Similarity	NPC201667
0.8217	Intermediate Similarity	NPC73413

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 NPC249836 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	254
0.1-0.2	907
0.2-0.3	1555
0.3-0.4	2625
0.4-0.5	1855
0.5-0.6	1186
0.6-0.7	608
0.7-0.8	148
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.856	High Similarity	NPD422	Phase 1
0.8397	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD4625	Phase 3
0.8281	Intermediate Similarity	NPD4749	Approved
0.8244	Intermediate Similarity	NPD4908	Phase 1
0.8203	Intermediate Similarity	NPD1608	Approved
0.8197	Intermediate Similarity	NPD5535	Approved
0.8129	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1610	Phase 2
0.812	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1548	Phase 1
0.8045	Intermediate Similarity	NPD3027	Phase 3
0.803	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD2797	Approved
0.8	Intermediate Similarity	NPD6671	Approved
0.7985	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD6100	Approved
0.7971	Intermediate Similarity	NPD6099	Approved
0.7969	Intermediate Similarity	NPD17	Approved
0.7939	Intermediate Similarity	NPD3225	Approved
0.791	Intermediate Similarity	NPD7095	Approved
0.7872	Intermediate Similarity	NPD3750	Approved
0.7868	Intermediate Similarity	NPD1613	Approved
0.7868	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD4060	Phase 1
0.7852	Intermediate Similarity	NPD3268	Approved
0.781	Intermediate Similarity	NPD5124	Phase 1
0.781	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD3496	Discontinued
0.7718	Intermediate Similarity	NPD7819	Suspended
0.7714	Intermediate Similarity	NPD1551	Phase 2
0.771	Intermediate Similarity	NPD1611	Approved
0.7692	Intermediate Similarity	NPD1778	Approved
0.7687	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7033	Discontinued
0.763	Intermediate Similarity	NPD2861	Phase 2
0.7616	Intermediate Similarity	NPD7768	Phase 2
0.7615	Intermediate Similarity	NPD5585	Approved
0.7612	Intermediate Similarity	NPD1203	Approved
0.7583	Intermediate Similarity	NPD1242	Phase 1
0.7576	Intermediate Similarity	NPD1535	Discovery
0.7574	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD968	Approved
0.7535	Intermediate Similarity	NPD5762	Approved
0.7535	Intermediate Similarity	NPD5763	Approved
0.7534	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD4750	Phase 3
0.7519	Intermediate Similarity	NPD1481	Phase 2
0.7518	Intermediate Similarity	NPD3748	Approved
0.7518	Intermediate Similarity	NPD4308	Phase 3
0.75	Intermediate Similarity	NPD3847	Discontinued
0.7483	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD4140	Approved
0.7481	Intermediate Similarity	NPD3266	Approved
0.7481	Intermediate Similarity	NPD3267	Approved
0.748	Intermediate Similarity	NPD7843	Approved
0.7467	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD2935	Discontinued
0.7464	Intermediate Similarity	NPD1296	Phase 2
0.7463	Intermediate Similarity	NPD2982	Phase 2
0.7463	Intermediate Similarity	NPD2983	Phase 2
0.7451	Intermediate Similarity	NPD7075	Discontinued
0.7445	Intermediate Similarity	NPD6832	Phase 2
0.7431	Intermediate Similarity	NPD1652	Phase 2
0.7429	Intermediate Similarity	NPD6355	Discontinued
0.7426	Intermediate Similarity	NPD6584	Phase 3
0.7424	Intermediate Similarity	NPD4626	Approved
0.7415	Intermediate Similarity	NPD7447	Phase 1
0.7413	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD8032	Phase 2
0.7407	Intermediate Similarity	NPD6696	Suspended
0.7405	Intermediate Similarity	NPD1894	Discontinued
0.7397	Intermediate Similarity	NPD6667	Approved
0.7397	Intermediate Similarity	NPD6666	Approved
0.7388	Intermediate Similarity	NPD2981	Phase 2
0.7388	Intermediate Similarity	NPD9717	Approved
0.7386	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1653	Approved
0.7379	Intermediate Similarity	NPD3892	Phase 2
0.7379	Intermediate Similarity	NPD4628	Phase 3
0.7377	Intermediate Similarity	NPD846	Approved
0.7377	Intermediate Similarity	NPD940	Approved
0.7376	Intermediate Similarity	NPD6653	Approved
0.7372	Intermediate Similarity	NPD3018	Phase 2
0.7368	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1549	Phase 2
0.7357	Intermediate Similarity	NPD1240	Approved
0.7351	Intermediate Similarity	NPD7411	Suspended
0.7347	Intermediate Similarity	NPD1511	Approved
0.7347	Intermediate Similarity	NPD6799	Approved
0.7343	Intermediate Similarity	NPD6032	Approved
0.7339	Intermediate Similarity	NPD9697	Approved
0.7338	Intermediate Similarity	NPD6798	Discontinued
0.7333	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4359	Approved
0.7333	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD2614	Approved
0.7313	Intermediate Similarity	NPD1091	Approved
0.731	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7157	Approved
0.7305	Intermediate Similarity	NPD4340	Discontinued
0.7303	Intermediate Similarity	NPD1934	Approved
0.7302	Intermediate Similarity	NPD2684	Approved
0.7297	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD5283	Phase 1
0.7286	Intermediate Similarity	NPD6233	Phase 2
0.7279	Intermediate Similarity	NPD1283	Approved
0.7273	Intermediate Similarity	NPD1510	Phase 2
0.7261	Intermediate Similarity	NPD7229	Phase 3
0.726	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2801	Approved
0.7254	Intermediate Similarity	NPD1607	Approved
0.725	Intermediate Similarity	NPD2859	Approved
0.725	Intermediate Similarity	NPD2860	Approved
0.7248	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1512	Approved
0.7234	Intermediate Similarity	NPD4307	Phase 2
0.723	Intermediate Similarity	NPD7213	Phase 3
0.723	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7212	Phase 2
0.7226	Intermediate Similarity	NPD3749	Approved
0.7226	Intermediate Similarity	NPD6971	Discontinued
0.7222	Intermediate Similarity	NPD2796	Approved
0.7219	Intermediate Similarity	NPD3226	Approved
0.7218	Intermediate Similarity	NPD5691	Approved
0.7214	Intermediate Similarity	NPD411	Approved
0.7213	Intermediate Similarity	NPD3020	Approved
0.7208	Intermediate Similarity	NPD5402	Approved
0.7208	Intermediate Similarity	NPD3817	Phase 2
0.7206	Intermediate Similarity	NPD6582	Phase 2
0.7206	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD6583	Phase 3
0.72	Intermediate Similarity	NPD5403	Approved
0.7197	Intermediate Similarity	NPD7199	Phase 2
0.719	Intermediate Similarity	NPD37	Approved
0.7183	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD447	Suspended
0.7179	Intermediate Similarity	NPD6234	Discontinued
0.7172	Intermediate Similarity	NPD6002	Phase 3
0.7172	Intermediate Similarity	NPD6005	Phase 3
0.7172	Intermediate Similarity	NPD7266	Discontinued
0.7172	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6004	Phase 3
0.7171	Intermediate Similarity	NPD6599	Discontinued
0.717	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD2934	Approved
0.7167	Intermediate Similarity	NPD2933	Approved
0.7164	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD4062	Phase 3
0.7161	Intermediate Similarity	NPD4965	Approved
0.7161	Intermediate Similarity	NPD3882	Suspended
0.7161	Intermediate Similarity	NPD4967	Phase 2
0.7161	Intermediate Similarity	NPD4966	Approved
0.7153	Intermediate Similarity	NPD2799	Discontinued
0.7153	Intermediate Similarity	NPD8651	Approved
0.7143	Intermediate Similarity	NPD5844	Phase 1
0.7143	Intermediate Similarity	NPD1465	Phase 2
0.7143	Intermediate Similarity	NPD5163	Phase 2
0.7143	Intermediate Similarity	NPD3134	Approved
0.7134	Intermediate Similarity	NPD6746	Phase 2
0.7132	Intermediate Similarity	NPD2231	Phase 2
0.7132	Intermediate Similarity	NPD228	Approved
0.7132	Intermediate Similarity	NPD2235	Phase 2
0.7113	Intermediate Similarity	NPD1558	Phase 1
0.7109	Intermediate Similarity	NPD3022	Approved
0.7109	Intermediate Similarity	NPD3021	Approved
0.7107	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6362	Approved
0.7092	Intermediate Similarity	NPD3764	Approved
0.7092	Intermediate Similarity	NPD2313	Discontinued
0.7087	Intermediate Similarity	NPD1358	Approved
0.7087	Intermediate Similarity	NPD290	Approved
0.7086	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7097	Phase 1
0.7083	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6801	Discontinued
0.7075	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1243	Approved
0.7068	Intermediate Similarity	NPD7644	Approved
0.7067	Intermediate Similarity	NPD5401	Approved
0.7067	Intermediate Similarity	NPD2533	Approved
0.7067	Intermediate Similarity	NPD2532	Approved
0.7067	Intermediate Similarity	NPD2534	Approved
0.7063	Intermediate Similarity	NPD230	Phase 1
0.7059	Intermediate Similarity	NPD1281	Approved
0.7055	Intermediate Similarity	NPD2346	Discontinued
0.7045	Intermediate Similarity	NPD709	Approved
0.7044	Intermediate Similarity	NPD6232	Discontinued
0.7042	Intermediate Similarity	NPD4870	Approved
0.7039	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7976	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4110	Phase 3

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