NPASS Compound

Structure

NPC474105 OpenBabel07101719242D 21 25 0 0 1 0 0 0 0 0999 V2000 -0.9628 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4814 -0.8338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6187 0.4814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4452 1.3417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8924 -1.5457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8924 1.5457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7849 1.0305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7849 -2.0610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4830 0.1273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6055 -1.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6341 -0.5839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4877 -0.1021 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1359 -0.9983 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8924 -0.5152 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6773 -0.5152 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0305 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 1.7849 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5356 -0.2456 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6773 -1.5457 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8338 1.5119 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 5 8 1 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 7 18 1 0 0 0 0 8 20 1 0 0 0 0 9 12 1 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 19 1 1 0 0 0 13 19 1 1 0 0 0 14 17 1 0 0 0 0 14 18 1 1 0 0 0 15 18 1 6 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 18 3 1 6 0 0 0 19 4 1 6 0 0 0 20 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.23
Volume:	317.848
LogP:	4.437
LogD:	4.101
LogS:	-4.54
# Rotatable Bonds:	0
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.622
Synthetic Accessibility Score:	6.015
Fsp3:	0.95
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:	-5.314
MDCK Permeability:	1.4477916010946501e-05
Pgp-inhibitor:	0.356
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.053
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.116
Plasma Protein Binding (PPB):	85.99088287353516%
Volume Distribution (VD):	0.86
Pgp-substrate:	9.59493637084961%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.681
CYP2C19-inhibitor:	0.132
CYP2C19-substrate:	0.911
CYP2C9-inhibitor:	0.188
CYP2C9-substrate:	0.358
CYP2D6-inhibitor:	0.063
CYP2D6-substrate:	0.449
CYP3A4-inhibitor:	0.87
CYP3A4-substrate:	0.363

ADMET: Excretion

Clearance (CL):	17.182
Half-life (T1/2):	0.502

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.619
Drug-inuced Liver Injury (DILI):	0.065
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.565
Maximum Recommended Daily Dose:	0.859
Skin Sensitization:	0.56
Carcinogencity:	0.39
Eye Corrosion:	0.45
Eye Irritation:	0.179
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC474105

Natural Product ID:	NPC474105
*Common Name:**	DVXUPVLGDAAEFK-WBKRPPKXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DVXUPVLGDAAEFK-WBKRPPKXSA-N
Standard InCHI:	InChI=1S/C20H30O/c1-17(2)14-5-8-20-10-13-12(19(13,4)11-20)9-15(20)18(14,3)7-6-16(17)21/h12-15H,5-11H2,1-4H3/t12-,13+,14+,15+,18-,19+,20+/m1/s1
SMILES:	CC1(C)[C@@H]2CC[C@]34C[C@H]5[C@@H](C[C@H]4[C@]2(C)CCC1=O)[C@]5(C)C3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461825
PubChem CID:	44566738
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane 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
NPO21790	Croton insularis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104505]
NPO12671	Croton zambesicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17547457]
NPO2026	Jungermannia exsertifolia	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20353194]
NPO12671	Croton zambesicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12671	Croton zambesicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21790	Croton insularis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12671	Croton zambesicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4
Others	2

Activity Type	# Activity
Cell Line	3
Organism	1
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	33500.0	nM	PMID[519963]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	131000.0	nM	PMID[519964]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	103000.0	nM	PMID[519964]
NPT177	Tissue	Aorta	Rattus norvegicus	IC50	>	80000.0	nM	PMID[519963]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	65.6	%	PMID[519963]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC90	=	173000.0	nM	PMID[519965]

☑ 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 NPC474105 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	559
0.1-0.2	12138
0.2-0.3	15067
0.3-0.4	6958
0.4-0.5	5407
0.5-0.6	2077
0.6-0.7	413
0.7-0.8	58
0.8-0.85	14
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9434	High Similarity	NPC184819
0.9259	High Similarity	NPC151464
0.9259	High Similarity	NPC143597
0.9245	High Similarity	NPC53245
0.9245	High Similarity	NPC288296
0.8525	High Similarity	NPC96812
0.8525	High Similarity	NPC107704
0.8525	High Similarity	NPC39462
0.8525	High Similarity	NPC189917
0.8525	High Similarity	NPC168824
0.8333	Intermediate Similarity	NPC274182
0.8269	Intermediate Similarity	NPC98246
0.8269	Intermediate Similarity	NPC285814
0.8269	Intermediate Similarity	NPC83187
0.8125	Intermediate Similarity	NPC477857
0.8125	Intermediate Similarity	NPC474962
0.807	Intermediate Similarity	NPC307063
0.8	Intermediate Similarity	NPC477856
0.8	Intermediate Similarity	NPC214770
0.7963	Intermediate Similarity	NPC293343
0.7963	Intermediate Similarity	NPC247786
0.7963	Intermediate Similarity	NPC258672
0.7937	Intermediate Similarity	NPC43300
0.7879	Intermediate Similarity	NPC473267
0.7812	Intermediate Similarity	NPC130459
0.7812	Intermediate Similarity	NPC474221
0.7812	Intermediate Similarity	NPC478180
0.7778	Intermediate Similarity	NPC294440
0.7761	Intermediate Similarity	NPC474123
0.7692	Intermediate Similarity	NPC473225
0.7667	Intermediate Similarity	NPC127798
0.7593	Intermediate Similarity	NPC131981
0.7593	Intermediate Similarity	NPC40249
0.7593	Intermediate Similarity	NPC173996
0.7536	Intermediate Similarity	NPC255650
0.7536	Intermediate Similarity	NPC273366
0.7463	Intermediate Similarity	NPC40574
0.7463	Intermediate Similarity	NPC108131
0.7463	Intermediate Similarity	NPC477850
0.7424	Intermediate Similarity	NPC20610
0.7391	Intermediate Similarity	NPC255021
0.7385	Intermediate Similarity	NPC42060
0.7385	Intermediate Similarity	NPC323005
0.7385	Intermediate Similarity	NPC477931
0.7385	Intermediate Similarity	NPC268736
0.7353	Intermediate Similarity	NPC151018
0.7353	Intermediate Similarity	NPC197701
0.7353	Intermediate Similarity	NPC110615
0.7353	Intermediate Similarity	NPC156277
0.7353	Intermediate Similarity	NPC58057
0.7353	Intermediate Similarity	NPC320549
0.7344	Intermediate Similarity	NPC128608
0.7324	Intermediate Similarity	NPC264602
0.7324	Intermediate Similarity	NPC475031
0.7313	Intermediate Similarity	NPC324607
0.7313	Intermediate Similarity	NPC182815
0.7313	Intermediate Similarity	NPC327728
0.7313	Intermediate Similarity	NPC196197
0.7313	Intermediate Similarity	NPC321732
0.7313	Intermediate Similarity	NPC213178
0.7313	Intermediate Similarity	NPC131892
0.7313	Intermediate Similarity	NPC6120
0.7286	Intermediate Similarity	NPC72444
0.7246	Intermediate Similarity	NPC232112
0.7246	Intermediate Similarity	NPC310766
0.7222	Intermediate Similarity	NPC478128
0.7206	Intermediate Similarity	NPC307176
0.7206	Intermediate Similarity	NPC159577
0.7206	Intermediate Similarity	NPC282593
0.7206	Intermediate Similarity	NPC476731
0.7206	Intermediate Similarity	NPC35734
0.7183	Intermediate Similarity	NPC69408
0.717	Intermediate Similarity	NPC18397
0.7164	Intermediate Similarity	NPC474954
0.7143	Intermediate Similarity	NPC254340
0.7143	Intermediate Similarity	NPC20017
0.7143	Intermediate Similarity	NPC270042
0.7143	Intermediate Similarity	NPC472854
0.7143	Intermediate Similarity	NPC159497
0.7123	Intermediate Similarity	NPC52951
0.7115	Intermediate Similarity	NPC45270
0.7115	Intermediate Similarity	NPC215118
0.7115	Intermediate Similarity	NPC59570
0.7115	Intermediate Similarity	NPC135077
0.7101	Intermediate Similarity	NPC305501
0.7101	Intermediate Similarity	NPC234707
0.7101	Intermediate Similarity	NPC115023
0.7101	Intermediate Similarity	NPC126642
0.7101	Intermediate Similarity	NPC472309
0.7101	Intermediate Similarity	NPC89310
0.7101	Intermediate Similarity	NPC470078
0.7059	Intermediate Similarity	NPC319671
0.7059	Intermediate Similarity	NPC64466
0.7059	Intermediate Similarity	NPC469941
0.7059	Intermediate Similarity	NPC476734
0.7059	Intermediate Similarity	NPC252032
0.7059	Intermediate Similarity	NPC139397
0.7042	Intermediate Similarity	NPC21220
0.7042	Intermediate Similarity	NPC125767
0.7042	Intermediate Similarity	NPC293803
0.7042	Intermediate Similarity	NPC195155
0.7042	Intermediate Similarity	NPC97534
0.7042	Intermediate Similarity	NPC472311
0.7042	Intermediate Similarity	NPC174964
0.7037	Intermediate Similarity	NPC171783
0.7	Intermediate Similarity	NPC303613
0.7	Intermediate Similarity	NPC474228
0.7	Intermediate Similarity	NPC251705
0.6957	Remote Similarity	NPC2634
0.6957	Remote Similarity	NPC265782
0.6957	Remote Similarity	NPC477929
0.6957	Remote Similarity	NPC260040
0.6957	Remote Similarity	NPC251929
0.6944	Remote Similarity	NPC472487
0.6944	Remote Similarity	NPC475742
0.6944	Remote Similarity	NPC472486
0.6944	Remote Similarity	NPC5767
0.6933	Remote Similarity	NPC77311
0.6933	Remote Similarity	NPC469745
0.6923	Remote Similarity	NPC472306
0.6901	Remote Similarity	NPC167702
0.6901	Remote Similarity	NPC280026
0.6901	Remote Similarity	NPC133922
0.6857	Remote Similarity	NPC54123
0.6857	Remote Similarity	NPC223187
0.6857	Remote Similarity	NPC469940
0.6857	Remote Similarity	NPC5701
0.6849	Remote Similarity	NPC470557
0.6849	Remote Similarity	NPC221420
0.6849	Remote Similarity	NPC477918
0.6849	Remote Similarity	NPC474404
0.6849	Remote Similarity	NPC91665
0.6849	Remote Similarity	NPC23884
0.6842	Remote Similarity	NPC477858
0.6818	Remote Similarity	NPC469662
0.6806	Remote Similarity	NPC24014
0.6806	Remote Similarity	NPC27349
0.6806	Remote Similarity	NPC212733
0.6806	Remote Similarity	NPC159789
0.68	Remote Similarity	NPC477851
0.6765	Remote Similarity	NPC220210
0.6765	Remote Similarity	NPC20181
0.6761	Remote Similarity	NPC470044
0.6761	Remote Similarity	NPC52667
0.6761	Remote Similarity	NPC470045
0.6757	Remote Similarity	NPC185465
0.6757	Remote Similarity	NPC63020
0.6753	Remote Similarity	NPC15821
0.6753	Remote Similarity	NPC472744
0.6731	Remote Similarity	NPC223315
0.6712	Remote Similarity	NPC20466
0.6712	Remote Similarity	NPC471046
0.6712	Remote Similarity	NPC4209
0.6711	Remote Similarity	NPC12933
0.6667	Remote Similarity	NPC281203
0.6667	Remote Similarity	NPC142754
0.6667	Remote Similarity	NPC31302
0.6667	Remote Similarity	NPC245029
0.6667	Remote Similarity	NPC477930
0.6667	Remote Similarity	NPC260319
0.6667	Remote Similarity	NPC215843
0.6667	Remote Similarity	NPC178025
0.6667	Remote Similarity	NPC202118
0.6667	Remote Similarity	NPC469724
0.6667	Remote Similarity	NPC296697
0.6667	Remote Similarity	NPC103647
0.6667	Remote Similarity	NPC39157
0.6667	Remote Similarity	NPC470956
0.6667	Remote Similarity	NPC31187
0.6667	Remote Similarity	NPC320144
0.6667	Remote Similarity	NPC2568
0.6667	Remote Similarity	NPC309852
0.6667	Remote Similarity	NPC192744
0.6667	Remote Similarity	NPC180777
0.6667	Remote Similarity	NPC474996
0.6667	Remote Similarity	NPC319909
0.6667	Remote Similarity	NPC201459
0.6667	Remote Similarity	NPC16287
0.6667	Remote Similarity	NPC82477
0.6667	Remote Similarity	NPC197238
0.6667	Remote Similarity	NPC475977
0.6667	Remote Similarity	NPC181743
0.6667	Remote Similarity	NPC100917
0.6623	Remote Similarity	NPC271163
0.6622	Remote Similarity	NPC477919
0.6622	Remote Similarity	NPC143133
0.6622	Remote Similarity	NPC212661
0.6622	Remote Similarity	NPC207010
0.6622	Remote Similarity	NPC298168
0.6622	Remote Similarity	NPC180199
0.6622	Remote Similarity	NPC471035
0.6622	Remote Similarity	NPC317913
0.6622	Remote Similarity	NPC66105
0.6622	Remote Similarity	NPC106078
0.6613	Remote Similarity	NPC200258
0.6582	Remote Similarity	NPC60350
0.6582	Remote Similarity	NPC76518
0.6579	Remote Similarity	NPC472853
0.6579	Remote Similarity	NPC474509
0.6579	Remote Similarity	NPC470609

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 NPC474105 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	589
0.1-0.2	5645
0.2-0.3	2181
0.3-0.4	360
0.4-0.5	244
0.5-0.6	94
0.6-0.7	30
0.7-0.8	7
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	NPD5360	Phase 3
0.7692	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD4224	Phase 2
0.7593	Intermediate Similarity	NPD345	Approved
0.7593	Intermediate Similarity	NPD344	Approved
0.7593	Intermediate Similarity	NPD343	Approved
0.75	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD4789	Approved
0.7353	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4758	Discontinued
0.7353	Intermediate Similarity	NPD6081	Approved
0.7313	Intermediate Similarity	NPD3698	Phase 2
0.7313	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD4747	Approved
0.7206	Intermediate Similarity	NPD4244	Approved
0.7206	Intermediate Similarity	NPD4245	Approved
0.7164	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5777	Approved
0.7059	Intermediate Similarity	NPD4137	Phase 3
0.6957	Remote Similarity	NPD4691	Approved
0.6901	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3703	Phase 2
0.6757	Remote Similarity	NPD5364	Discontinued
0.6712	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD4687	Approved
0.6667	Remote Similarity	NPD5733	Approved
0.6667	Remote Similarity	NPD4058	Approved
0.6622	Remote Similarity	NPD6116	Phase 1
0.662	Remote Similarity	NPD5276	Approved
0.6575	Remote Similarity	NPD3702	Approved
0.6533	Remote Similarity	NPD3671	Phase 1
0.6533	Remote Similarity	NPD6697	Approved
0.6533	Remote Similarity	NPD6115	Approved
0.6533	Remote Similarity	NPD6118	Approved
0.6533	Remote Similarity	NPD4777	Suspended
0.6533	Remote Similarity	NPD4776	Phase 2
0.6533	Remote Similarity	NPD6114	Approved
0.6329	Remote Similarity	NPD4788	Approved
0.6316	Remote Similarity	NPD3617	Approved
0.6203	Remote Similarity	NPD4221	Approved
0.6203	Remote Similarity	NPD4223	Phase 3
0.6076	Remote Similarity	NPD4139	Approved
0.6076	Remote Similarity	NPD4692	Approved
0.6049	Remote Similarity	NPD4197	Approved
0.6049	Remote Similarity	NPD4786	Approved
0.6026	Remote Similarity	NPD7155	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3667	Approved
0.5976	Remote Similarity	NPD5329	Approved
0.5976	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD5205	Approved
0.5904	Remote Similarity	NPD4138	Approved
0.5904	Remote Similarity	NPD6098	Approved
0.5904	Remote Similarity	NPD4693	Phase 3
0.5904	Remote Similarity	NPD4689	Approved
0.5904	Remote Similarity	NPD4690	Approved
0.5904	Remote Similarity	NPD4688	Approved
0.5854	Remote Similarity	NPD3665	Phase 1
0.5854	Remote Similarity	NPD3133	Approved
0.5854	Remote Similarity	NPD3666	Approved
0.5854	Remote Similarity	NPD3668	Phase 3
0.5795	Remote Similarity	NPD6001	Approved
0.5765	Remote Similarity	NPD6672	Approved
0.5765	Remote Similarity	NPD5737	Approved
0.5765	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD5208	Approved
0.5732	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.573	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7146	Approved
0.5714	Remote Similarity	NPD5690	Phase 2
0.5714	Remote Similarity	NPD6684	Approved
0.5714	Remote Similarity	NPD6409	Approved
0.5714	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3618	Phase 1
0.5714	Remote Similarity	NPD7521	Approved
0.5714	Remote Similarity	NPD5330	Approved
0.5714	Remote Similarity	NPD4694	Approved
0.5714	Remote Similarity	NPD7334	Approved
0.5714	Remote Similarity	NPD5280	Approved
0.5698	Remote Similarity	NPD6904	Approved
0.5698	Remote Similarity	NPD6080	Approved
0.5698	Remote Similarity	NPD6673	Approved
0.5698	Remote Similarity	NPD5328	Approved
0.5698	Remote Similarity	NPD4753	Phase 2
0.5682	Remote Similarity	NPD5133	Approved
0.5679	Remote Similarity	NPD8028	Phase 2
0.5676	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.56	Remote Similarity	NPD4787	Phase 1

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