NPASS Compound

Structure

NPC140521 OpenBabel07101718322D 35 36 0 0 0 0 0 0 0 0999 V2000 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 -12.9904 7.5000 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 -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 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 -13.8564 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 0.0000 0.0000 0.0000 C 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 -14.7224 7.5000 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 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 3 2 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 25 1 0 0 0 0 17 26 1 0 0 0 0 18 25 2 0 0 0 0 18 27 1 0 0 0 0 19 25 1 0 0 0 0 19 28 2 0 0 0 0 20 26 2 0 0 0 0 20 29 1 0 0 0 0 21 26 1 0 0 0 0 21 30 2 0 0 0 0 22 27 2 0 0 0 0 22 28 1 0 0 0 0 23 29 2 0 0 0 0 23 30 1 0 0 0 0 24 31 2 0 0 0 0 24 35 1 0 0 0 0 27 32 1 0 0 0 0 28 33 1 0 0 0 0 29 34 1 0 0 0 0 30 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.3
Volume:	533.183
LogP:	7.191
LogD:	4.469
LogS:	-2.431
# Rotatable Bonds:	18
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.093
Synthetic Accessibility Score:	2.698
Fsp3:	0.5
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:	-5.126
MDCK Permeability:	2.3227963538374752e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.194
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	100.28975677490234%
Volume Distribution (VD):	1.35
Pgp-substrate:	0.5126007795333862%

ADMET: Metabolism

CYP1A2-inhibitor:	0.626
CYP1A2-substrate:	0.177
CYP2C19-inhibitor:	0.86
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.251
CYP2C9-substrate:	0.993
CYP2D6-inhibitor:	0.973
CYP2D6-substrate:	0.719
CYP3A4-inhibitor:	0.686
CYP3A4-substrate:	0.066

ADMET: Excretion

Clearance (CL):	5.279
Half-life (T1/2):	0.933

ADMET: Toxicity

hERG Blockers:	0.326
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.981
Carcinogencity:	0.025
Eye Corrosion:	0.036
Eye Irritation:	0.944
Respiratory Toxicity:	0.708

Download Data

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

Natural Product: NPC140521

Natural Product ID:	NPC140521
*Common Name:**	Oncostemonol B
IUPAC Name:	[3-[(Z)-16-(3,5-dihydroxyphenyl)hexadec-8-enyl]-5-hydroxyphenyl] acetate
Synonyms:	oncostemonol B
Standard InCHIKey:	CATXXSJNZBRPTC-IHWYPQMZSA-N
Standard InCHI:	InChI=1S/C30H42O5/c1-24(31)35-30-21-26(20-29(34)23-30)17-15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-25-18-27(32)22-28(33)19-25/h2-3,18-23,32-34H,4-17H2,1H3/b3-2-
SMILES:	CC(=O)Oc1cc(CCCCCCC/C=CCCCCCCCc2cc(cc(c2)O)O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458522
PubChem CID:	11755009
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	=	10.2	ug.mL-1	PMID[452376]

☑ 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 NPC140521 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	NPC249836
0.9831	High Similarity	NPC78446
0.9316	High Similarity	NPC471498
0.9316	High Similarity	NPC471503
0.9153	High Similarity	NPC470759
0.9153	High Similarity	NPC127894
0.9153	High Similarity	NPC15860
0.9153	High Similarity	NPC219070
0.9083	High Similarity	NPC473290
0.9083	High Similarity	NPC471504
0.9068	High Similarity	NPC114064
0.8983	High Similarity	NPC53906
0.8898	High Similarity	NPC276737
0.8898	High Similarity	NPC22610
0.8898	High Similarity	NPC32463
0.8833	High Similarity	NPC474933
0.8833	High Similarity	NPC69261
0.8833	High Similarity	NPC33270
0.8828	High Similarity	NPC142530
0.8803	High Similarity	NPC255068
0.88	High Similarity	NPC168259
0.8769	High Similarity	NPC131950
0.876	High Similarity	NPC245120
0.876	High Similarity	NPC474635
0.875	High Similarity	NPC123559
0.875	High Similarity	NPC150624
0.875	High Similarity	NPC141090
0.8712	High Similarity	NPC474886
0.8712	High Similarity	NPC476171
0.8699	High Similarity	NPC218753
0.8692	High Similarity	NPC474810
0.8689	High Similarity	NPC184302
0.8667	High Similarity	NPC167934
0.8667	High Similarity	NPC808
0.8661	High Similarity	NPC470699
0.8661	High Similarity	NPC243688
0.8636	High Similarity	NPC471719
0.8629	High Similarity	NPC187868
0.8629	High Similarity	NPC476633
0.8629	High Similarity	NPC52247
0.8626	High Similarity	NPC309744
0.8626	High Similarity	NPC111635
0.8607	High Similarity	NPC190514
0.8583	High Similarity	NPC181361
0.8583	High Similarity	NPC228287
0.8583	High Similarity	NPC180508
0.8561	High Similarity	NPC252095
0.856	High Similarity	NPC18128
0.856	High Similarity	NPC77789
0.8559	High Similarity	NPC168657
0.8559	High Similarity	NPC2682
0.8559	High Similarity	NPC94045
0.8538	High Similarity	NPC147317
0.8538	High Similarity	NPC472590
0.8538	High Similarity	NPC8899
0.8538	High Similarity	NPC250727
0.8537	High Similarity	NPC137294
0.8537	High Similarity	NPC85895
0.8525	High Similarity	NPC195466
0.8525	High Similarity	NPC244816
0.8525	High Similarity	NPC50521
0.8525	High Similarity	NPC221549
0.8516	High Similarity	NPC46978
0.8516	High Similarity	NPC210355
0.8504	High Similarity	NPC244495
0.8504	High Similarity	NPC93219
0.8492	Intermediate Similarity	NPC282496
0.8492	Intermediate Similarity	NPC136319
0.8492	Intermediate Similarity	NPC38761
0.8492	Intermediate Similarity	NPC233526
0.8492	Intermediate Similarity	NPC76465
0.8492	Intermediate Similarity	NPC315807
0.8473	Intermediate Similarity	NPC5423
0.8473	Intermediate Similarity	NPC469611
0.8462	Intermediate Similarity	NPC79184
0.8462	Intermediate Similarity	NPC307042
0.845	Intermediate Similarity	NPC474651
0.845	Intermediate Similarity	NPC185066
0.845	Intermediate Similarity	NPC219923
0.845	Intermediate Similarity	NPC469453
0.845	Intermediate Similarity	NPC210674
0.845	Intermediate Similarity	NPC474623
0.8443	Intermediate Similarity	NPC54507
0.8443	Intermediate Similarity	NPC85292
0.8443	Intermediate Similarity	NPC229147
0.8443	Intermediate Similarity	NPC203113
0.8438	Intermediate Similarity	NPC230479
0.8438	Intermediate Similarity	NPC50315
0.8438	Intermediate Similarity	NPC283049
0.8438	Intermediate Similarity	NPC26879
0.8433	Intermediate Similarity	NPC38874
0.8425	Intermediate Similarity	NPC228972
0.8425	Intermediate Similarity	NPC270030
0.8425	Intermediate Similarity	NPC122792
0.8417	Intermediate Similarity	NPC280606
0.8413	Intermediate Similarity	NPC302211
0.8413	Intermediate Similarity	NPC36016
0.8413	Intermediate Similarity	NPC100099
0.8413	Intermediate Similarity	NPC74137
0.8409	Intermediate Similarity	NPC469610
0.8409	Intermediate Similarity	NPC31849
0.8406	Intermediate Similarity	NPC125617
0.84	Intermediate Similarity	NPC302107
0.84	Intermediate Similarity	NPC102639
0.8394	Intermediate Similarity	NPC110067
0.8394	Intermediate Similarity	NPC34245
0.8394	Intermediate Similarity	NPC7439
0.8394	Intermediate Similarity	NPC91492
0.8394	Intermediate Similarity	NPC256555
0.839	Intermediate Similarity	NPC245115
0.8385	Intermediate Similarity	NPC93962
0.8385	Intermediate Similarity	NPC222108
0.8385	Intermediate Similarity	NPC16577
0.8385	Intermediate Similarity	NPC474289
0.8385	Intermediate Similarity	NPC96719
0.8376	Intermediate Similarity	NPC39097
0.8376	Intermediate Similarity	NPC118286
0.8376	Intermediate Similarity	NPC109691
0.8376	Intermediate Similarity	NPC470700
0.8376	Intermediate Similarity	NPC39664
0.8376	Intermediate Similarity	NPC302681
0.8372	Intermediate Similarity	NPC194841
0.8372	Intermediate Similarity	NPC473221
0.8372	Intermediate Similarity	NPC474670
0.8372	Intermediate Similarity	NPC121740
0.8372	Intermediate Similarity	NPC474821
0.8372	Intermediate Similarity	NPC224774
0.8372	Intermediate Similarity	NPC257947
0.8372	Intermediate Similarity	NPC66331
0.8372	Intermediate Similarity	NPC258567
0.8361	Intermediate Similarity	NPC185541
0.8361	Intermediate Similarity	NPC464
0.8359	Intermediate Similarity	NPC475169
0.8359	Intermediate Similarity	NPC476254
0.8359	Intermediate Similarity	NPC203133
0.8359	Intermediate Similarity	NPC221077
0.8359	Intermediate Similarity	NPC131397
0.8359	Intermediate Similarity	NPC105925
0.8359	Intermediate Similarity	NPC298757
0.8359	Intermediate Similarity	NPC472093
0.8359	Intermediate Similarity	NPC285040
0.8359	Intermediate Similarity	NPC113495
0.8359	Intermediate Similarity	NPC251855
0.8359	Intermediate Similarity	NPC17809
0.8359	Intermediate Similarity	NPC117214
0.8359	Intermediate Similarity	NPC57490
0.8359	Intermediate Similarity	NPC193544
0.8359	Intermediate Similarity	NPC116907
0.8359	Intermediate Similarity	NPC188022
0.8359	Intermediate Similarity	NPC102540
0.8359	Intermediate Similarity	NPC208950
0.8359	Intermediate Similarity	NPC17943
0.8359	Intermediate Similarity	NPC233410
0.8359	Intermediate Similarity	NPC103420
0.8346	Intermediate Similarity	NPC96940
0.8345	Intermediate Similarity	NPC29577
0.8345	Intermediate Similarity	NPC475896
0.8333	Intermediate Similarity	NPC470752
0.8333	Intermediate Similarity	NPC194277
0.8333	Intermediate Similarity	NPC471824
0.8333	Intermediate Similarity	NPC54972
0.8333	Intermediate Similarity	NPC212965
0.8333	Intermediate Similarity	NPC36732
0.8333	Intermediate Similarity	NPC296920
0.8333	Intermediate Similarity	NPC75713
0.8333	Intermediate Similarity	NPC90520
0.8321	Intermediate Similarity	NPC476399
0.8321	Intermediate Similarity	NPC472338
0.8321	Intermediate Similarity	NPC262606
0.8321	Intermediate Similarity	NPC474617
0.832	Intermediate Similarity	NPC247553
0.8308	Intermediate Similarity	NPC38664
0.8308	Intermediate Similarity	NPC474616
0.8308	Intermediate Similarity	NPC474636
0.8308	Intermediate Similarity	NPC274717
0.8308	Intermediate Similarity	NPC53986
0.8306	Intermediate Similarity	NPC131118
0.8305	Intermediate Similarity	NPC54844
0.8305	Intermediate Similarity	NPC35543
0.8296	Intermediate Similarity	NPC105493
0.8296	Intermediate Similarity	NPC131198
0.8296	Intermediate Similarity	NPC124149
0.8295	Intermediate Similarity	NPC82299
0.8295	Intermediate Similarity	NPC276212
0.8295	Intermediate Similarity	NPC101894
0.8295	Intermediate Similarity	NPC474632
0.8291	Intermediate Similarity	NPC134829
0.8291	Intermediate Similarity	NPC246056
0.8286	Intermediate Similarity	NPC170239
0.8286	Intermediate Similarity	NPC237208
0.8286	Intermediate Similarity	NPC275125
0.8286	Intermediate Similarity	NPC97937
0.8284	Intermediate Similarity	NPC311430
0.8284	Intermediate Similarity	NPC224941
0.8281	Intermediate Similarity	NPC159132
0.8281	Intermediate Similarity	NPC73413
0.8281	Intermediate Similarity	NPC246648
0.8281	Intermediate Similarity	NPC134195
0.8281	Intermediate Similarity	NPC197351
0.8281	Intermediate Similarity	NPC86502

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 NPC140521 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
0.8629	High Similarity	NPD422	Phase 1
0.8462	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD4625	Phase 3
0.8346	Intermediate Similarity	NPD4749	Approved
0.8308	Intermediate Similarity	NPD4908	Phase 1
0.8268	Intermediate Similarity	NPD1608	Approved
0.8264	Intermediate Similarity	NPD5535	Approved
0.8189	Intermediate Similarity	NPD1610	Phase 2
0.8188	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8168	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD1548	Phase 1
0.8106	Intermediate Similarity	NPD3027	Phase 3
0.8092	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD2797	Approved
0.8065	Intermediate Similarity	NPD6671	Approved
0.8045	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8031	Intermediate Similarity	NPD17	Approved
0.8029	Intermediate Similarity	NPD6099	Approved
0.8029	Intermediate Similarity	NPD6100	Approved
0.8	Intermediate Similarity	NPD3225	Approved
0.797	Intermediate Similarity	NPD7095	Approved
0.7929	Intermediate Similarity	NPD3750	Approved
0.7926	Intermediate Similarity	NPD1613	Approved
0.7926	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD4060	Phase 1
0.791	Intermediate Similarity	NPD3268	Approved
0.7868	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD5124	Phase 1
0.7829	Intermediate Similarity	NPD3496	Discontinued
0.777	Intermediate Similarity	NPD1551	Phase 2
0.7769	Intermediate Similarity	NPD1611	Approved
0.7752	Intermediate Similarity	NPD1778	Approved
0.7744	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD7033	Discontinued
0.7687	Intermediate Similarity	NPD2861	Phase 2
0.7674	Intermediate Similarity	NPD5585	Approved
0.7669	Intermediate Similarity	NPD1203	Approved
0.7651	Intermediate Similarity	NPD7819	Suspended
0.7647	Intermediate Similarity	NPD1242	Phase 1
0.7634	Intermediate Similarity	NPD1535	Discovery
0.763	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD968	Approved
0.7589	Intermediate Similarity	NPD5762	Approved
0.7589	Intermediate Similarity	NPD5763	Approved
0.7586	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD4750	Phase 3
0.7576	Intermediate Similarity	NPD1481	Phase 2
0.7571	Intermediate Similarity	NPD4308	Phase 3
0.7571	Intermediate Similarity	NPD3748	Approved
0.7557	Intermediate Similarity	NPD3847	Discontinued
0.755	Intermediate Similarity	NPD7768	Phase 2
0.7537	Intermediate Similarity	NPD3266	Approved
0.7537	Intermediate Similarity	NPD3267	Approved
0.7536	Intermediate Similarity	NPD4140	Approved
0.7535	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD2982	Phase 2
0.7519	Intermediate Similarity	NPD2983	Phase 2
0.7518	Intermediate Similarity	NPD2935	Discontinued
0.7518	Intermediate Similarity	NPD1296	Phase 2
0.7517	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7075	Discontinued
0.75	Intermediate Similarity	NPD6832	Phase 2
0.7483	Intermediate Similarity	NPD1652	Phase 2
0.7482	Intermediate Similarity	NPD6355	Discontinued
0.7481	Intermediate Similarity	NPD6584	Phase 3
0.7481	Intermediate Similarity	NPD4626	Approved
0.7466	Intermediate Similarity	NPD7447	Phase 1
0.7465	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD6696	Suspended
0.7462	Intermediate Similarity	NPD1894	Discontinued
0.7448	Intermediate Similarity	NPD6666	Approved
0.7448	Intermediate Similarity	NPD6667	Approved
0.7444	Intermediate Similarity	NPD9717	Approved
0.7444	Intermediate Similarity	NPD2981	Phase 2
0.7438	Intermediate Similarity	NPD846	Approved
0.7438	Intermediate Similarity	NPD940	Approved
0.7434	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1653	Approved
0.7431	Intermediate Similarity	NPD4628	Phase 3
0.7431	Intermediate Similarity	NPD3892	Phase 2
0.7429	Intermediate Similarity	NPD6653	Approved
0.7426	Intermediate Similarity	NPD3018	Phase 2
0.7417	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1549	Phase 2
0.741	Intermediate Similarity	NPD1240	Approved
0.7402	Intermediate Similarity	NPD7843	Approved
0.74	Intermediate Similarity	NPD7411	Suspended
0.7398	Intermediate Similarity	NPD9697	Approved
0.7397	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD6799	Approved
0.7397	Intermediate Similarity	NPD1511	Approved
0.7394	Intermediate Similarity	NPD6032	Approved
0.7391	Intermediate Similarity	NPD6798	Discontinued
0.7388	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD4359	Approved
0.7372	Intermediate Similarity	NPD2614	Approved
0.7368	Intermediate Similarity	NPD1091	Approved
0.7364	Intermediate Similarity	NPD7157	Approved
0.7361	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD2684	Approved
0.7357	Intermediate Similarity	NPD4340	Discontinued
0.7351	Intermediate Similarity	NPD1934	Approved
0.7347	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD5283	Phase 1
0.7338	Intermediate Similarity	NPD6233	Phase 2
0.7338	Intermediate Similarity	NPD8032	Phase 2
0.7333	Intermediate Similarity	NPD1283	Approved
0.7324	Intermediate Similarity	NPD1510	Phase 2
0.7311	Intermediate Similarity	NPD2860	Approved
0.7311	Intermediate Similarity	NPD2859	Approved
0.731	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7229	Phase 3
0.7305	Intermediate Similarity	NPD1607	Approved
0.7303	Intermediate Similarity	NPD2801	Approved
0.7297	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1512	Approved
0.7286	Intermediate Similarity	NPD4307	Phase 2
0.7279	Intermediate Similarity	NPD7213	Phase 3
0.7279	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7212	Phase 2
0.7273	Intermediate Similarity	NPD3749	Approved
0.7273	Intermediate Similarity	NPD2796	Approved
0.7273	Intermediate Similarity	NPD5691	Approved
0.7273	Intermediate Similarity	NPD3020	Approved
0.7273	Intermediate Similarity	NPD6971	Discontinued
0.7267	Intermediate Similarity	NPD3226	Approved
0.7267	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD411	Approved
0.7259	Intermediate Similarity	NPD6582	Phase 2
0.7259	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD6583	Phase 3
0.7255	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5402	Approved
0.7255	Intermediate Similarity	NPD3817	Phase 2
0.7248	Intermediate Similarity	NPD5403	Approved
0.7244	Intermediate Similarity	NPD7199	Phase 2
0.7237	Intermediate Similarity	NPD37	Approved
0.7234	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD447	Suspended
0.7227	Intermediate Similarity	NPD2933	Approved
0.7227	Intermediate Similarity	NPD2934	Approved
0.7226	Intermediate Similarity	NPD6234	Discontinued
0.7222	Intermediate Similarity	NPD6005	Phase 3
0.7222	Intermediate Similarity	NPD6004	Phase 3
0.7222	Intermediate Similarity	NPD7266	Discontinued
0.7222	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6002	Phase 3
0.7219	Intermediate Similarity	NPD6599	Discontinued
0.7218	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD4062	Phase 3
0.7208	Intermediate Similarity	NPD4967	Phase 2
0.7208	Intermediate Similarity	NPD3882	Suspended
0.7208	Intermediate Similarity	NPD4965	Approved
0.7208	Intermediate Similarity	NPD4966	Approved
0.7203	Intermediate Similarity	NPD2799	Discontinued
0.72	Intermediate Similarity	NPD3134	Approved
0.7194	Intermediate Similarity	NPD5163	Phase 2
0.719	Intermediate Similarity	NPD1465	Phase 2
0.7188	Intermediate Similarity	NPD5844	Phase 1
0.7188	Intermediate Similarity	NPD228	Approved
0.7185	Intermediate Similarity	NPD2231	Phase 2
0.7185	Intermediate Similarity	NPD2235	Phase 2
0.7179	Intermediate Similarity	NPD6746	Phase 2
0.7165	Intermediate Similarity	NPD3021	Approved
0.7165	Intermediate Similarity	NPD3022	Approved
0.7163	Intermediate Similarity	NPD1558	Phase 1
0.7153	Intermediate Similarity	NPD6362	Approved
0.7152	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1358	Approved
0.7143	Intermediate Similarity	NPD290	Approved
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD3764	Approved
0.7133	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7097	Phase 1
0.7133	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6801	Discontinued
0.7123	Intermediate Similarity	NPD1243	Approved
0.7123	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7644	Approved
0.7114	Intermediate Similarity	NPD5401	Approved
0.7114	Intermediate Similarity	NPD2533	Approved
0.7114	Intermediate Similarity	NPD2532	Approved
0.7114	Intermediate Similarity	NPD2534	Approved
0.7113	Intermediate Similarity	NPD230	Phase 1
0.7111	Intermediate Similarity	NPD1281	Approved
0.7107	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2346	Discontinued
0.7099	Intermediate Similarity	NPD709	Approved
0.7092	Intermediate Similarity	NPD4870	Approved
0.709	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6232	Discontinued
0.7086	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD8651	Approved
0.7075	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7075	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