NPASS Compound

Structure

CID228911 OpenBabel06191716022D 27 30 0 0 1 0 0 0 0 0999 V2000 -1.5232 -2.9632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2065 -3.0538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8990 0.0353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1564 0.9877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8013 -1.5091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9319 -2.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2247 -2.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3570 -0.8812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9986 0.0523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1778 -1.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9319 -0.5176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3145 -3.8557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6322 -2.5092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5900 -0.9157 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9319 -2.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5799 -1.5106 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6390 -1.2247 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2247 -1.2247 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5900 -2.5338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6390 -2.2247 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2588 -0.9659 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9319 -0.5176 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7058 -4.6491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8990 -3.4848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 2 15 1 0 0 0 0 6 7 1 0 0 0 0 6 17 2 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 24 1 0 0 0 0 10 11 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 25 1 0 0 0 0 14 17 1 0 0 0 0 14 26 2 0 0 0 0 16 3 1 1 0 0 0 16 19 1 0 0 0 0 18 15 1 1 0 0 0 18 23 1 0 0 0 0 19 13 1 1 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 20 25 1 1 0 0 0 21 22 1 0 0 0 0 21 27 2 0 0 0 0 22 17 1 1 0 0 0 23 24 1 6 0 0 0 24 4 1 6 0 0 0 25 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.27
Volume:	413.765
LogP:	5.047
LogD:	4.192
LogS:	-5.118
# Rotatable Bonds:	2
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.458
Synthetic Accessibility Score:	5.14
Fsp3:	0.76
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.618
MDCK Permeability:	2.1089308575028554e-05
Pgp-inhibitor:	0.762
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.815
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.853
Plasma Protein Binding (PPB):	62.291561126708984%
Volume Distribution (VD):	2.903
Pgp-substrate:	17.068321228027344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.644
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.873
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.966
CYP3A4-substrate:	0.728

ADMET: Excretion

Clearance (CL):	20.627
Half-life (T1/2):	0.019

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.164
Drug-inuced Liver Injury (DILI):	0.181
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.896
Maximum Recommended Daily Dose:	0.874
Skin Sensitization:	0.732
Carcinogencity:	0.897
Eye Corrosion:	0.615
Eye Irritation:	0.104
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC228911

Natural Product ID:	NPC228911
*Common Name:**	Variecolin
IUPAC Name:	n.a.
Synonyms:	Variecolin
Standard InCHIKey:	XAYQASOMEVLRKN-NOJNFTMQSA-N
Standard InCHI:	InChI=1S/C25H36O2/c1-15(2)18-8-9-24(4)10-11-25(5)13-19-16(3)12-21(27)22(19)17(14-26)6-7-20(25)23(18)24/h6,14,16,18-20,22-23H,1,7-13H2,2-5H3/b17-6-/t16-,18+,19-,20-,22-,23-,24-,25+/m0/s1
SMILES:	C=C(C)[C@H]1CC[C@@]2(C)CC[C@]3(C)C[C@H]4[C@@H](C)CC(=O)[C@H]4C(=CC[C@H]3[C@H]12)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519317
PubChem CID:	6480205
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids

*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
NPO31540	Aspergillus variecolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jo00010a040]
NPO31502	Emericella aurantiobrunnea	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11045446]
NPO30877	Phoma	Genus	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11099218]
NPO30877	Phoma	Genus	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11671521]
NPO31502	Emericella aurantiobrunnea	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497939]
NPO31540	Aspergillus variecolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17896816]
NPO31540	Aspergillus variecolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17965475]
NPO30877	Phoma	Genus	Didymellaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21247198]
NPO30877	Phoma	Genus	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]

☑ 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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT236	Individual Protein	C-C chemokine receptor type 5	Homo sapiens	IC50	=	9000.0	nM	PMID[510262]

☑ 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 NPC228911 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	178
0.1-0.2	2102
0.2-0.3	13681
0.3-0.4	11992
0.4-0.5	8578
0.5-0.6	4867
0.6-0.7	1149
0.7-0.8	141
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.859	High Similarity	NPC90965
0.859	High Similarity	NPC170793
0.8481	Intermediate Similarity	NPC474509
0.8442	Intermediate Similarity	NPC469796
0.8442	Intermediate Similarity	NPC469793
0.84	Intermediate Similarity	NPC304983
0.8289	Intermediate Similarity	NPC474228
0.8289	Intermediate Similarity	NPC303613
0.8243	Intermediate Similarity	NPC155198
0.8182	Intermediate Similarity	NPC309852
0.8158	Intermediate Similarity	NPC474562
0.8108	Intermediate Similarity	NPC290350
0.8108	Intermediate Similarity	NPC4370
0.8052	Intermediate Similarity	NPC470045
0.8052	Intermediate Similarity	NPC251705
0.8052	Intermediate Similarity	NPC470044
0.8026	Intermediate Similarity	NPC260040
0.8026	Intermediate Similarity	NPC35734
0.8026	Intermediate Similarity	NPC159577
0.8026	Intermediate Similarity	NPC265782
0.8026	Intermediate Similarity	NPC251929
0.8026	Intermediate Similarity	NPC2634
0.8026	Intermediate Similarity	NPC307176
0.8026	Intermediate Similarity	NPC282593
0.8	Intermediate Similarity	NPC115515
0.7975	Intermediate Similarity	NPC69408
0.7949	Intermediate Similarity	NPC128346
0.7949	Intermediate Similarity	NPC219232
0.7949	Intermediate Similarity	NPC211641
0.7949	Intermediate Similarity	NPC474797
0.7949	Intermediate Similarity	NPC474796
0.7949	Intermediate Similarity	NPC329866
0.7949	Intermediate Similarity	NPC255021
0.7949	Intermediate Similarity	NPC159497
0.7945	Intermediate Similarity	NPC212210
0.7922	Intermediate Similarity	NPC115023
0.7922	Intermediate Similarity	NPC54123
0.7922	Intermediate Similarity	NPC234707
0.7922	Intermediate Similarity	NPC305501
0.7895	Intermediate Similarity	NPC162867
0.7895	Intermediate Similarity	NPC61702
0.7895	Intermediate Similarity	NPC139397
0.7867	Intermediate Similarity	NPC475523
0.7848	Intermediate Similarity	NPC293803
0.7848	Intermediate Similarity	NPC255650
0.7808	Intermediate Similarity	NPC165695
0.7808	Intermediate Similarity	NPC472306
0.7792	Intermediate Similarity	NPC40574
0.7778	Intermediate Similarity	NPC270042
0.7778	Intermediate Similarity	NPC25853
0.7763	Intermediate Similarity	NPC20610
0.7738	Intermediate Similarity	NPC470165
0.7733	Intermediate Similarity	NPC176171
0.7703	Intermediate Similarity	NPC473902
0.7703	Intermediate Similarity	NPC52449
0.7703	Intermediate Similarity	NPC169275
0.7692	Intermediate Similarity	NPC5701
0.7671	Intermediate Similarity	NPC213152
0.7671	Intermediate Similarity	NPC60565
0.7662	Intermediate Similarity	NPC256846
0.7662	Intermediate Similarity	NPC182815
0.7639	Intermediate Similarity	NPC259261
0.7614	Intermediate Similarity	NPC41217
0.7564	Intermediate Similarity	NPC214770
0.7564	Intermediate Similarity	NPC477856
0.7561	Intermediate Similarity	NPC82635
0.7561	Intermediate Similarity	NPC469996
0.7532	Intermediate Similarity	NPC260474
0.7532	Intermediate Similarity	NPC188292
0.7529	Intermediate Similarity	NPC41539
0.7528	Intermediate Similarity	NPC2946
0.7528	Intermediate Similarity	NPC191684
0.75	Intermediate Similarity	NPC266295
0.75	Intermediate Similarity	NPC94991
0.75	Intermediate Similarity	NPC30215
0.7468	Intermediate Similarity	NPC470078
0.7468	Intermediate Similarity	NPC223187
0.7442	Intermediate Similarity	NPC473246
0.7442	Intermediate Similarity	NPC214043
0.7442	Intermediate Similarity	NPC85774
0.7436	Intermediate Similarity	NPC477857
0.7432	Intermediate Similarity	NPC475795
0.7412	Intermediate Similarity	NPC3511
0.7412	Intermediate Similarity	NPC142253
0.7412	Intermediate Similarity	NPC472239
0.7407	Intermediate Similarity	NPC473171
0.7403	Intermediate Similarity	NPC176107
0.7386	Intermediate Similarity	NPC93778
0.7381	Intermediate Similarity	NPC472478
0.7375	Intermediate Similarity	NPC52667
0.7368	Intermediate Similarity	NPC251118
0.7368	Intermediate Similarity	NPC183422
0.7363	Intermediate Similarity	NPC250575
0.7361	Intermediate Similarity	NPC267626
0.7361	Intermediate Similarity	NPC230823
0.7361	Intermediate Similarity	NPC49575
0.7361	Intermediate Similarity	NPC55004
0.7356	Intermediate Similarity	NPC472940
0.7356	Intermediate Similarity	NPC472931
0.7356	Intermediate Similarity	NPC469948
0.7349	Intermediate Similarity	NPC470052
0.7333	Intermediate Similarity	NPC49946
0.7333	Intermediate Similarity	NPC126993
0.7333	Intermediate Similarity	NPC32285
0.7333	Intermediate Similarity	NPC167256
0.7333	Intermediate Similarity	NPC306168
0.7326	Intermediate Similarity	NPC474790
0.7326	Intermediate Similarity	NPC474976
0.7317	Intermediate Similarity	NPC19907
0.7317	Intermediate Similarity	NPC474463
0.7308	Intermediate Similarity	NPC87141
0.7308	Intermediate Similarity	NPC310992
0.7303	Intermediate Similarity	NPC477710
0.7297	Intermediate Similarity	NPC127582
0.7294	Intermediate Similarity	NPC4166
0.7294	Intermediate Similarity	NPC477372
0.7273	Intermediate Similarity	NPC145879
0.7273	Intermediate Similarity	NPC118648
0.7273	Intermediate Similarity	NPC475022
0.7273	Intermediate Similarity	NPC323005
0.7273	Intermediate Similarity	NPC474733
0.7273	Intermediate Similarity	NPC474778
0.7273	Intermediate Similarity	NPC222613
0.7273	Intermediate Similarity	NPC31564
0.7273	Intermediate Similarity	NPC92327
0.7273	Intermediate Similarity	NPC474732
0.7262	Intermediate Similarity	NPC472490
0.725	Intermediate Similarity	NPC181204
0.725	Intermediate Similarity	NPC190035
0.7241	Intermediate Similarity	NPC178025
0.7241	Intermediate Similarity	NPC87552
0.7241	Intermediate Similarity	NPC181743
0.7241	Intermediate Similarity	NPC237712
0.7241	Intermediate Similarity	NPC475100
0.7241	Intermediate Similarity	NPC16287
0.7237	Intermediate Similarity	NPC475124
0.7237	Intermediate Similarity	NPC285371
0.7229	Intermediate Similarity	NPC470557
0.7229	Intermediate Similarity	NPC91665
0.7215	Intermediate Similarity	NPC469677
0.7209	Intermediate Similarity	NPC469805
0.7209	Intermediate Similarity	NPC469804
0.7209	Intermediate Similarity	NPC321289
0.7209	Intermediate Similarity	NPC470813
0.7209	Intermediate Similarity	NPC472867
0.7209	Intermediate Similarity	NPC311092
0.7209	Intermediate Similarity	NPC142683
0.7209	Intermediate Similarity	NPC100297
0.7209	Intermediate Similarity	NPC327969
0.7209	Intermediate Similarity	NPC240302
0.7209	Intermediate Similarity	NPC320514
0.72	Intermediate Similarity	NPC97322
0.7195	Intermediate Similarity	NPC65650
0.7191	Intermediate Similarity	NPC475740
0.7191	Intermediate Similarity	NPC58063
0.7179	Intermediate Similarity	NPC193770
0.7174	Intermediate Similarity	NPC229976
0.7162	Intermediate Similarity	NPC276764
0.7162	Intermediate Similarity	NPC472304
0.716	Intermediate Similarity	NPC144947
0.7159	Intermediate Similarity	NPC11711
0.7159	Intermediate Similarity	NPC8571
0.7159	Intermediate Similarity	NPC60350
0.7159	Intermediate Similarity	NPC29447
0.7159	Intermediate Similarity	NPC470223
0.7143	Intermediate Similarity	NPC268039
0.7143	Intermediate Similarity	NPC183283
0.7143	Intermediate Similarity	NPC477711
0.7143	Intermediate Similarity	NPC470329
0.7126	Intermediate Similarity	NPC175410
0.7126	Intermediate Similarity	NPC470046
0.7126	Intermediate Similarity	NPC470047
0.7126	Intermediate Similarity	NPC3856
0.7126	Intermediate Similarity	NPC307258
0.7126	Intermediate Similarity	NPC474748
0.7126	Intermediate Similarity	NPC279639
0.7125	Intermediate Similarity	NPC246722
0.7125	Intermediate Similarity	NPC151045
0.7123	Intermediate Similarity	NPC115385
0.7111	Intermediate Similarity	NPC471722
0.7108	Intermediate Similarity	NPC215481
0.7105	Intermediate Similarity	NPC288253
0.7093	Intermediate Similarity	NPC90055
0.7089	Intermediate Similarity	NPC469688
0.7079	Intermediate Similarity	NPC94755
0.7079	Intermediate Similarity	NPC470051
0.7079	Intermediate Similarity	NPC470050
0.7079	Intermediate Similarity	NPC195640
0.7079	Intermediate Similarity	NPC72133
0.7079	Intermediate Similarity	NPC168248
0.7073	Intermediate Similarity	NPC20025
0.7065	Intermediate Similarity	NPC23217
0.7065	Intermediate Similarity	NPC190442
0.7065	Intermediate Similarity	NPC272746
0.7065	Intermediate Similarity	NPC218301
0.7065	Intermediate Similarity	NPC476187
0.7059	Intermediate Similarity	NPC215843
0.7059	Intermediate Similarity	NPC477371
0.7059	Intermediate Similarity	NPC190211
0.7051	Intermediate Similarity	NPC39462

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 NPC228911 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	2506
0.2-0.3	4695
0.3-0.4	1217
0.4-0.5	270
0.5-0.6	206
0.6-0.7	89
0.7-0.8	9
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
0.8026	Intermediate Similarity	NPD4747	Approved
0.8026	Intermediate Similarity	NPD4691	Approved
0.7949	Intermediate Similarity	NPD5733	Approved
0.7895	Intermediate Similarity	NPD4137	Phase 3
0.7722	Intermediate Similarity	NPD4687	Approved
0.7722	Intermediate Similarity	NPD4058	Approved
0.7692	Intermediate Similarity	NPD5276	Approved
0.7308	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6903	Approved
0.7111	Intermediate Similarity	NPD6672	Approved
0.7111	Intermediate Similarity	NPD5737	Approved
0.7079	Intermediate Similarity	NPD6409	Approved
0.7079	Intermediate Similarity	NPD7521	Approved
0.7079	Intermediate Similarity	NPD6684	Approved
0.7079	Intermediate Similarity	NPD5330	Approved
0.7079	Intermediate Similarity	NPD7334	Approved
0.7079	Intermediate Similarity	NPD7146	Approved
0.7065	Intermediate Similarity	NPD6079	Approved
0.7045	Intermediate Similarity	NPD3665	Phase 1
0.7045	Intermediate Similarity	NPD4786	Approved
0.7045	Intermediate Similarity	NPD3133	Approved
0.7045	Intermediate Similarity	NPD3666	Approved
0.7033	Intermediate Similarity	NPD5328	Approved
0.7011	Intermediate Similarity	NPD4223	Phase 3
0.7011	Intermediate Similarity	NPD4221	Approved
0.6966	Remote Similarity	NPD5329	Approved
0.6947	Remote Similarity	NPD4697	Phase 3
0.6932	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5279	Phase 3
0.6889	Remote Similarity	NPD3618	Phase 1
0.6889	Remote Similarity	NPD5690	Phase 2
0.6854	Remote Similarity	NPD4197	Approved
0.6848	Remote Similarity	NPD4753	Phase 2
0.6818	Remote Similarity	NPD3667	Approved
0.68	Remote Similarity	NPD287	Approved
0.6742	Remote Similarity	NPD4788	Approved
0.6703	Remote Similarity	NPD4693	Phase 3
0.6703	Remote Similarity	NPD4689	Approved
0.6703	Remote Similarity	NPD4688	Approved
0.6703	Remote Similarity	NPD5205	Approved
0.6703	Remote Similarity	NPD4690	Approved
0.6703	Remote Similarity	NPD4138	Approved
0.6703	Remote Similarity	NPD4694	Approved
0.6703	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6673	Approved
0.6667	Remote Similarity	NPD3668	Phase 3
0.6667	Remote Similarity	NPD6904	Approved
0.6632	Remote Similarity	NPD4202	Approved
0.6632	Remote Similarity	NPD6399	Phase 3
0.6598	Remote Similarity	NPD5221	Approved
0.6598	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5222	Approved
0.6596	Remote Similarity	NPD5207	Approved
0.6559	Remote Similarity	NPD5208	Approved
0.6552	Remote Similarity	NPD3617	Approved
0.6531	Remote Similarity	NPD5173	Approved
0.6531	Remote Similarity	NPD6083	Phase 2
0.6531	Remote Similarity	NPD6084	Phase 2
0.6526	Remote Similarity	NPD6050	Approved
0.6522	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6098	Approved
0.6517	Remote Similarity	NPD8028	Phase 2
0.6495	Remote Similarity	NPD5695	Phase 3
0.6477	Remote Similarity	NPD4195	Approved
0.6444	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5692	Phase 3
0.6404	Remote Similarity	NPD4695	Discontinued
0.64	Remote Similarity	NPD5285	Approved
0.64	Remote Similarity	NPD5286	Approved
0.64	Remote Similarity	NPD4696	Approved
0.6392	Remote Similarity	NPD6001	Approved
0.6364	Remote Similarity	NPD4755	Approved
0.6364	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5694	Approved
0.6354	Remote Similarity	NPD5281	Approved
0.6354	Remote Similarity	NPD5693	Phase 1
0.6354	Remote Similarity	NPD5284	Approved
0.6337	Remote Similarity	NPD5223	Approved
0.63	Remote Similarity	NPD5696	Approved
0.6286	Remote Similarity	NPD7320	Approved
0.6275	Remote Similarity	NPD5211	Phase 2
0.6275	Remote Similarity	NPD5225	Approved
0.6275	Remote Similarity	NPD4633	Approved
0.6275	Remote Similarity	NPD5224	Approved
0.6275	Remote Similarity	NPD5226	Approved
0.625	Remote Similarity	NPD4096	Approved
0.6238	Remote Similarity	NPD4700	Approved
0.6224	Remote Similarity	NPD7900	Approved
0.6224	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5174	Approved
0.6214	Remote Similarity	NPD5175	Approved
0.6186	Remote Similarity	NPD7515	Phase 2
0.617	Remote Similarity	NPD4519	Discontinued
0.617	Remote Similarity	NPD4623	Approved
0.6154	Remote Similarity	NPD4139	Approved
0.6154	Remote Similarity	NPD4692	Approved
0.6154	Remote Similarity	NPD5141	Approved
0.6132	Remote Similarity	NPD6881	Approved
0.6132	Remote Similarity	NPD6899	Approved
0.6122	Remote Similarity	NPD5133	Approved
0.6111	Remote Similarity	NPD6649	Approved
0.6111	Remote Similarity	NPD6650	Approved
0.6105	Remote Similarity	NPD3573	Approved
0.6095	Remote Similarity	NPD6008	Approved
0.6095	Remote Similarity	NPD5739	Approved
0.6095	Remote Similarity	NPD6402	Approved
0.6095	Remote Similarity	NPD6675	Approved
0.6095	Remote Similarity	NPD7128	Approved
0.6075	Remote Similarity	NPD6373	Approved
0.6075	Remote Similarity	NPD6372	Approved
0.6064	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD1694	Approved
0.6061	Remote Similarity	NPD7748	Approved
0.6058	Remote Similarity	NPD4754	Approved
0.6058	Remote Similarity	NPD6052	Approved
0.6042	Remote Similarity	NPD4518	Approved
0.604	Remote Similarity	NPD7902	Approved
0.6038	Remote Similarity	NPD5697	Approved
0.6024	Remote Similarity	NPD7331	Phase 2
0.6023	Remote Similarity	NPD6942	Approved
0.6023	Remote Similarity	NPD7339	Approved
0.6019	Remote Similarity	NPD7102	Approved
0.6019	Remote Similarity	NPD7290	Approved
0.6019	Remote Similarity	NPD6883	Approved
0.6	Remote Similarity	NPD5654	Approved
0.6	Remote Similarity	NPD6922	Approved
0.6	Remote Similarity	NPD6923	Approved
0.5981	Remote Similarity	NPD6011	Approved
0.5981	Remote Similarity	NPD4729	Approved
0.5981	Remote Similarity	NPD5168	Approved
0.5981	Remote Similarity	NPD5128	Approved
0.5981	Remote Similarity	NPD4730	Approved
0.5972	Remote Similarity	NPD345	Approved
0.5972	Remote Similarity	NPD343	Approved
0.5972	Remote Similarity	NPD344	Approved
0.5963	Remote Similarity	NPD6617	Approved
0.5963	Remote Similarity	NPD6869	Approved
0.5963	Remote Similarity	NPD6847	Approved
0.5963	Remote Similarity	NPD8130	Phase 1
0.5962	Remote Similarity	NPD5091	Approved
0.5943	Remote Similarity	NPD4768	Approved
0.5943	Remote Similarity	NPD4767	Approved
0.593	Remote Similarity	NPD7143	Approved
0.593	Remote Similarity	NPD7144	Approved
0.5926	Remote Similarity	NPD6012	Approved
0.5926	Remote Similarity	NPD6014	Approved
0.5926	Remote Similarity	NPD6013	Approved
0.5922	Remote Similarity	NPD6404	Discontinued
0.5918	Remote Similarity	NPD5785	Approved
0.5909	Remote Similarity	NPD8297	Approved
0.5909	Remote Similarity	NPD6926	Approved
0.5909	Remote Similarity	NPD6882	Approved
0.5909	Remote Similarity	NPD6924	Approved
0.5904	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD5363	Approved
0.5888	Remote Similarity	NPD6614	Approved
0.5888	Remote Similarity	NPD6412	Phase 2
0.5888	Remote Similarity	NPD5701	Approved
0.5882	Remote Similarity	NPD5959	Approved
0.5872	Remote Similarity	NPD4634	Approved
0.5872	Remote Similarity	NPD5250	Approved
0.5872	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD5248	Approved
0.5872	Remote Similarity	NPD5135	Approved
0.5872	Remote Similarity	NPD5247	Approved
0.5872	Remote Similarity	NPD5251	Approved
0.5872	Remote Similarity	NPD5249	Phase 3
0.5872	Remote Similarity	NPD5169	Approved
0.587	Remote Similarity	NPD7525	Registered
0.587	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7151	Approved
0.5862	Remote Similarity	NPD7150	Approved
0.5862	Remote Similarity	NPD4243	Approved
0.5862	Remote Similarity	NPD7152	Approved
0.5859	Remote Similarity	NPD8034	Phase 2
0.5859	Remote Similarity	NPD8035	Phase 2
0.5851	Remote Similarity	NPD5362	Discontinued
0.5825	Remote Similarity	NPD7638	Approved
0.5818	Remote Similarity	NPD5215	Approved
0.5818	Remote Similarity	NPD5127	Approved
0.5818	Remote Similarity	NPD5216	Approved
0.5818	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD5217	Approved
0.5816	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.58	Remote Similarity	NPD7631	Approved
0.5784	Remote Similarity	NPD7732	Phase 3
0.5778	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD6933	Approved
0.5769	Remote Similarity	NPD7640	Approved
0.5769	Remote Similarity	NPD7639	Approved
0.5752	Remote Similarity	NPD6868	Approved
0.5747	Remote Similarity	NPD4789	Approved
0.5743	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.573	Remote Similarity	NPD4785	Approved
0.573	Remote Similarity	NPD4784	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