NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	218.17
Volume:	251.764
LogP:	3.488
LogD:	2.887
LogS:	-4.144
# Rotatable Bonds:	1
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.61
Synthetic Accessibility Score:	4.557
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.74
MDCK Permeability:	1.938384048116859e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.054
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	89.31090545654297%
Volume Distribution (VD):	1.338
Pgp-substrate:	9.188299179077148%

ADMET: Metabolism

CYP1A2-inhibitor:	0.108
CYP1A2-substrate:	0.76
CYP2C19-inhibitor:	0.505
CYP2C19-substrate:	0.895
CYP2C9-inhibitor:	0.165
CYP2C9-substrate:	0.366
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.57
CYP3A4-inhibitor:	0.124
CYP3A4-substrate:	0.505

ADMET: Excretion

Clearance (CL):	10.799
Half-life (T1/2):	0.523

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.577
Drug-inuced Liver Injury (DILI):	0.296
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.204
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.932
Carcinogencity:	0.813
Eye Corrosion:	0.798
Eye Irritation:	0.808
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC213152

Natural Product ID:	NPC213152
*Common Name:**	Solavetivone
IUPAC Name:	(3R,5S,6R)-6,10-dimethyl-3-prop-1-en-2-ylspiro[4.5]dec-9-en-8-one
Synonyms:	Solavetivone
Standard InCHIKey:	FGCUSSRGQNHZRW-UMVBOHGHSA-N
Standard InCHI:	InChI=1S/C15H22O/c1-10(2)13-5-6-15(9-13)11(3)7-14(16)8-12(15)4/h7,12-13H,1,5-6,8-9H2,2-4H3/t12-,13-,15-/m1/s1
SMILES:	C=C(C)[C@@H]1CC[C@@]2(C1)C(=CC(=O)C[C@H]2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465907
PubChem CID:	442399
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11816-015-0350-y]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)89267-5]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)90945-1]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11559179]
NPO12170	Solanum indicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575964]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12882150]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15666542]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17520525]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18001808]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20954721]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22966846]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23479199]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24704449]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26967731]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	trunk bark	n.a.	PMID[556731]
NPO14489	Hyoscyamus albus	Species	Solanaceae	Eukaryota	Hairy roots	n.a.	n.a.	PMID[9868154]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Tuber	n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Tubers	n.a.		Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12170	Solanum indicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14489	Hyoscyamus albus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16093	Achillea atrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12170	Solanum indicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25348	Metapochonia suchlasporia	Species	Clavicipitaceae	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	1
MIC	2

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	=	100000.0	nM	PMID[519123]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	100.0	ug.mL-1	PMID[519124]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	100.0	ug.mL-1	PMID[519124]

☑ 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 NPC213152 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	174
0.1-0.2	2677
0.2-0.3	15768
0.3-0.4	12229
0.4-0.5	7267
0.5-0.6	3465
0.6-0.7	917
0.7-0.8	158
0.8-0.85	20
0.85-0.9	15
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC212210
0.9167	High Similarity	NPC165695
0.9153	High Similarity	NPC127582
0.8889	High Similarity	NPC475523
0.8833	High Similarity	NPC25853
0.8814	High Similarity	NPC94991
0.8814	High Similarity	NPC30215
0.8814	High Similarity	NPC266295
0.8769	High Similarity	NPC159577
0.8769	High Similarity	NPC35734
0.8769	High Similarity	NPC282593
0.8769	High Similarity	NPC307176
0.871	High Similarity	NPC6697
0.871	High Similarity	NPC475124
0.871	High Similarity	NPC285371
0.8667	High Similarity	NPC472304
0.8667	High Similarity	NPC259261
0.8667	High Similarity	NPC276764
0.8644	High Similarity	NPC267626
0.8644	High Similarity	NPC49575
0.8644	High Similarity	NPC55004
0.8636	High Similarity	NPC115023
0.8615	High Similarity	NPC139397
0.8548	High Similarity	NPC472306
0.8548	High Similarity	NPC288253
0.8548	High Similarity	NPC32285
0.8507	High Similarity	NPC470045
0.8507	High Similarity	NPC474228
0.8507	High Similarity	NPC251705
0.8507	High Similarity	NPC303613
0.8507	High Similarity	NPC470044
0.85	High Similarity	NPC56905
0.85	High Similarity	NPC311852
0.85	High Similarity	NPC170799
0.85	High Similarity	NPC308108
0.85	High Similarity	NPC27610
0.8485	Intermediate Similarity	NPC260040
0.8485	Intermediate Similarity	NPC265782
0.8485	Intermediate Similarity	NPC251929
0.8485	Intermediate Similarity	NPC2634
0.8462	Intermediate Similarity	NPC20610
0.8413	Intermediate Similarity	NPC473902
0.8387	Intermediate Similarity	NPC475795
0.8382	Intermediate Similarity	NPC309852
0.8361	Intermediate Similarity	NPC143834
0.8358	Intermediate Similarity	NPC234707
0.8358	Intermediate Similarity	NPC54123
0.8358	Intermediate Similarity	NPC5701
0.8333	Intermediate Similarity	NPC182815
0.8333	Intermediate Similarity	NPC256846
0.8333	Intermediate Similarity	NPC115385
0.8333	Intermediate Similarity	NPC230823
0.8281	Intermediate Similarity	NPC251118
0.8276	Intermediate Similarity	NPC268564
0.8276	Intermediate Similarity	NPC23117
0.8261	Intermediate Similarity	NPC293803
0.8254	Intermediate Similarity	NPC202118
0.8254	Intermediate Similarity	NPC197238
0.8246	Intermediate Similarity	NPC64866
0.8209	Intermediate Similarity	NPC151045
0.8209	Intermediate Similarity	NPC246722
0.8182	Intermediate Similarity	NPC87141
0.8182	Intermediate Similarity	NPC188292
0.8182	Intermediate Similarity	NPC155198
0.8182	Intermediate Similarity	NPC260474
0.8182	Intermediate Similarity	NPC310992
0.8154	Intermediate Similarity	NPC323005
0.8143	Intermediate Similarity	NPC69408
0.8125	Intermediate Similarity	NPC469662
0.8116	Intermediate Similarity	NPC255021
0.8095	Intermediate Similarity	NPC60565
0.8088	Intermediate Similarity	NPC181204
0.8088	Intermediate Similarity	NPC470078
0.8088	Intermediate Similarity	NPC304983
0.8088	Intermediate Similarity	NPC305501
0.807	Intermediate Similarity	NPC32351
0.807	Intermediate Similarity	NPC116906
0.8065	Intermediate Similarity	NPC285594
0.8065	Intermediate Similarity	NPC96551
0.8033	Intermediate Similarity	NPC192427
0.8	Intermediate Similarity	NPC470329
0.8	Intermediate Similarity	NPC200258
0.7969	Intermediate Similarity	NPC167256
0.7966	Intermediate Similarity	NPC14002
0.7966	Intermediate Similarity	NPC474141
0.7941	Intermediate Similarity	NPC477856
0.7941	Intermediate Similarity	NPC214770
0.7937	Intermediate Similarity	NPC270042
0.7931	Intermediate Similarity	NPC236623
0.7879	Intermediate Similarity	NPC176171
0.7879	Intermediate Similarity	NPC92327
0.7869	Intermediate Similarity	NPC20603
0.7869	Intermediate Similarity	NPC473733
0.7857	Intermediate Similarity	NPC474797
0.7857	Intermediate Similarity	NPC329866
0.7857	Intermediate Similarity	NPC474796
0.7833	Intermediate Similarity	NPC5626
0.7826	Intermediate Similarity	NPC474562
0.7826	Intermediate Similarity	NPC223187
0.7826	Intermediate Similarity	NPC190035
0.7812	Intermediate Similarity	NPC97322
0.7808	Intermediate Similarity	NPC170793
0.7808	Intermediate Similarity	NPC90965
0.7794	Intermediate Similarity	NPC61702
0.7794	Intermediate Similarity	NPC162867
0.7761	Intermediate Similarity	NPC4370
0.7761	Intermediate Similarity	NPC176107
0.7761	Intermediate Similarity	NPC290350
0.7746	Intermediate Similarity	NPC255650
0.7746	Intermediate Similarity	NPC473171
0.7742	Intermediate Similarity	NPC193695
0.7714	Intermediate Similarity	NPC130016
0.7714	Intermediate Similarity	NPC109576
0.7714	Intermediate Similarity	NPC180015
0.7714	Intermediate Similarity	NPC56747
0.7705	Intermediate Similarity	NPC275472
0.7703	Intermediate Similarity	NPC474509
0.7681	Intermediate Similarity	NPC40574
0.7671	Intermediate Similarity	NPC469996
0.7671	Intermediate Similarity	NPC228911
0.7667	Intermediate Similarity	NPC296311
0.7647	Intermediate Similarity	NPC142754
0.7647	Intermediate Similarity	NPC39157
0.7647	Intermediate Similarity	NPC82477
0.7647	Intermediate Similarity	NPC296697
0.7639	Intermediate Similarity	NPC469793
0.7639	Intermediate Similarity	NPC469796
0.7627	Intermediate Similarity	NPC27438
0.7619	Intermediate Similarity	NPC60772
0.76	Intermediate Similarity	NPC477372
0.7576	Intermediate Similarity	NPC4638
0.7571	Intermediate Similarity	NPC133253
0.7571	Intermediate Similarity	NPC21944
0.7571	Intermediate Similarity	NPC225467
0.7541	Intermediate Similarity	NPC250539
0.7541	Intermediate Similarity	NPC63396
0.7541	Intermediate Similarity	NPC202850
0.7536	Intermediate Similarity	NPC286814
0.75	Intermediate Similarity	NPC3511
0.75	Intermediate Similarity	NPC65650
0.75	Intermediate Similarity	NPC476346
0.75	Intermediate Similarity	NPC320514
0.75	Intermediate Similarity	NPC193347
0.75	Intermediate Similarity	NPC220210
0.75	Intermediate Similarity	NPC20181
0.75	Intermediate Similarity	NPC114236
0.75	Intermediate Similarity	NPC142253
0.75	Intermediate Similarity	NPC472239
0.7467	Intermediate Similarity	NPC45495
0.7467	Intermediate Similarity	NPC472478
0.7458	Intermediate Similarity	NPC176819
0.7458	Intermediate Similarity	NPC228776
0.7458	Intermediate Similarity	NPC163984
0.7458	Intermediate Similarity	NPC58970
0.7432	Intermediate Similarity	NPC470052
0.7432	Intermediate Similarity	NPC82635
0.7414	Intermediate Similarity	NPC91962
0.7403	Intermediate Similarity	NPC41539
0.7397	Intermediate Similarity	NPC1254
0.7397	Intermediate Similarity	NPC473223
0.7397	Intermediate Similarity	NPC470525
0.7397	Intermediate Similarity	NPC263582
0.7397	Intermediate Similarity	NPC180886
0.7391	Intermediate Similarity	NPC469688
0.7377	Intermediate Similarity	NPC69898
0.7377	Intermediate Similarity	NPC295777
0.7377	Intermediate Similarity	NPC37644
0.7377	Intermediate Similarity	NPC45283
0.7368	Intermediate Similarity	NPC136150
0.7361	Intermediate Similarity	NPC20025
0.7353	Intermediate Similarity	NPC43300
0.7353	Intermediate Similarity	NPC96812
0.7353	Intermediate Similarity	NPC168824
0.7353	Intermediate Similarity	NPC39462
0.7353	Intermediate Similarity	NPC107704
0.7353	Intermediate Similarity	NPC189917
0.7333	Intermediate Similarity	NPC7232
0.7333	Intermediate Similarity	NPC472490
0.7333	Intermediate Similarity	NPC477371
0.7313	Intermediate Similarity	NPC150162
0.7308	Intermediate Similarity	NPC214043
0.7308	Intermediate Similarity	NPC237712
0.7308	Intermediate Similarity	NPC144258
0.7308	Intermediate Similarity	NPC473246
0.7308	Intermediate Similarity	NPC85774
0.7308	Intermediate Similarity	NPC87552
0.7297	Intermediate Similarity	NPC257666
0.7297	Intermediate Similarity	NPC472300
0.7297	Intermediate Similarity	NPC165711
0.7297	Intermediate Similarity	NPC91665
0.7297	Intermediate Similarity	NPC97377
0.7297	Intermediate Similarity	NPC266193
0.7288	Intermediate Similarity	NPC145311
0.7286	Intermediate Similarity	NPC477857
0.7286	Intermediate Similarity	NPC469677
0.7273	Intermediate Similarity	NPC327969
0.7273	Intermediate Similarity	NPC472867
0.7273	Intermediate Similarity	NPC321289
0.726	Intermediate Similarity	NPC77501
0.726	Intermediate Similarity	NPC251435

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 NPC213152 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	2955
0.2-0.3	4299
0.3-0.4	1162
0.4-0.5	299
0.5-0.6	183
0.6-0.7	65
0.7-0.8	8
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8769	High Similarity	NPD4747	Approved
0.8636	High Similarity	NPD5276	Approved
0.8615	High Similarity	NPD4137	Phase 3
0.85	High Similarity	NPD287	Approved
0.8485	Intermediate Similarity	NPD4691	Approved
0.8382	Intermediate Similarity	NPD5733	Approved
0.8382	Intermediate Similarity	NPD4687	Approved
0.8182	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD4058	Approved
0.75	Intermediate Similarity	NPD4221	Approved
0.75	Intermediate Similarity	NPD4223	Phase 3
0.7308	Intermediate Similarity	NPD4197	Approved
0.7215	Intermediate Similarity	NPD5329	Approved
0.7179	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4138	Approved
0.7125	Intermediate Similarity	NPD5205	Approved
0.7125	Intermediate Similarity	NPD4694	Approved
0.7125	Intermediate Similarity	NPD4689	Approved
0.7125	Intermediate Similarity	NPD4693	Phase 3
0.7125	Intermediate Similarity	NPD5690	Phase 2
0.7125	Intermediate Similarity	NPD5280	Approved
0.7125	Intermediate Similarity	NPD4690	Approved
0.7125	Intermediate Similarity	NPD5279	Phase 3
0.7125	Intermediate Similarity	NPD4688	Approved
0.7089	Intermediate Similarity	NPD3666	Approved
0.7089	Intermediate Similarity	NPD3665	Phase 1
0.7089	Intermediate Similarity	NPD3133	Approved
0.7013	Intermediate Similarity	NPD4695	Discontinued
0.6974	Remote Similarity	NPD3617	Approved
0.6951	Remote Similarity	NPD5737	Approved
0.6951	Remote Similarity	NPD6672	Approved
0.6951	Remote Similarity	NPD5208	Approved
0.6914	Remote Similarity	NPD6409	Approved
0.6914	Remote Similarity	NPD3618	Phase 1
0.6914	Remote Similarity	NPD7334	Approved
0.6914	Remote Similarity	NPD5330	Approved
0.6914	Remote Similarity	NPD7146	Approved
0.6914	Remote Similarity	NPD6684	Approved
0.6914	Remote Similarity	NPD7521	Approved
0.6875	Remote Similarity	NPD4786	Approved
0.6867	Remote Similarity	NPD6080	Approved
0.6867	Remote Similarity	NPD4753	Phase 2
0.6867	Remote Similarity	NPD6673	Approved
0.6867	Remote Similarity	NPD6904	Approved
0.6867	Remote Similarity	NPD5328	Approved
0.6857	Remote Similarity	NPD7331	Phase 2
0.6835	Remote Similarity	NPD3667	Approved
0.6786	Remote Similarity	NPD4096	Approved
0.6786	Remote Similarity	NPD5692	Phase 3
0.6786	Remote Similarity	NPD5207	Approved
0.6747	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6903	Approved
0.6747	Remote Similarity	NPD4518	Approved
0.6709	Remote Similarity	NPD8028	Phase 2
0.6707	Remote Similarity	NPD6098	Approved
0.6707	Remote Similarity	NPD4623	Approved
0.6707	Remote Similarity	NPD4519	Discontinued
0.6707	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6079	Approved
0.6706	Remote Similarity	NPD5694	Approved
0.6706	Remote Similarity	NPD5693	Phase 1
0.6706	Remote Similarity	NPD5284	Approved
0.6706	Remote Similarity	NPD5281	Approved
0.6706	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD3668	Phase 3
0.6667	Remote Similarity	NPD4195	Approved
0.6628	Remote Similarity	NPD4202	Approved
0.6552	Remote Similarity	NPD6001	Approved
0.65	Remote Similarity	NPD4692	Approved
0.65	Remote Similarity	NPD4139	Approved
0.6479	Remote Similarity	NPD7341	Phase 2
0.6477	Remote Similarity	NPD5210	Approved
0.6477	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5695	Phase 3
0.6477	Remote Similarity	NPD4629	Approved
0.6437	Remote Similarity	NPD5133	Approved
0.6429	Remote Similarity	NPD3573	Approved
0.642	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5222	Approved
0.6404	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4697	Phase 3
0.6404	Remote Similarity	NPD5221	Approved
0.6393	Remote Similarity	NPD343	Approved
0.6393	Remote Similarity	NPD345	Approved
0.6393	Remote Similarity	NPD344	Approved
0.6333	Remote Similarity	NPD6084	Phase 2
0.6333	Remote Similarity	NPD6083	Phase 2
0.6333	Remote Similarity	NPD4755	Approved
0.6333	Remote Similarity	NPD5173	Approved
0.6329	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD5654	Approved
0.6286	Remote Similarity	NPD4193	Approved
0.6286	Remote Similarity	NPD4194	Approved
0.6286	Remote Similarity	NPD4192	Approved
0.6286	Remote Similarity	NPD4191	Approved
0.6264	Remote Similarity	NPD5696	Approved
0.625	Remote Similarity	NPD6399	Phase 3
0.6196	Remote Similarity	NPD4700	Approved
0.6196	Remote Similarity	NPD5285	Approved
0.6196	Remote Similarity	NPD4696	Approved
0.6196	Remote Similarity	NPD5286	Approved
0.619	Remote Similarity	NPD1694	Approved
0.6184	Remote Similarity	NPD4243	Approved
0.6173	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5959	Approved
0.6145	Remote Similarity	NPD4788	Approved
0.6136	Remote Similarity	NPD7515	Phase 2
0.6129	Remote Similarity	NPD5223	Approved
0.6119	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5224	Approved
0.6064	Remote Similarity	NPD4633	Approved
0.6064	Remote Similarity	NPD5091	Approved
0.6064	Remote Similarity	NPD5211	Phase 2
0.6064	Remote Similarity	NPD5225	Approved
0.6064	Remote Similarity	NPD5226	Approved
0.6026	Remote Similarity	NPD4784	Approved
0.6026	Remote Similarity	NPD4785	Approved
0.6	Remote Similarity	NPD7900	Approved
0.6	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4754	Approved
0.6	Remote Similarity	NPD5175	Approved
0.6	Remote Similarity	NPD5174	Approved
0.6	Remote Similarity	NPD6052	Approved
0.6	Remote Similarity	NPD1696	Phase 3
0.6	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7748	Approved
0.5972	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD6942	Approved
0.5949	Remote Similarity	NPD5275	Approved
0.5949	Remote Similarity	NPD7339	Approved
0.5949	Remote Similarity	NPD4190	Phase 3
0.5949	Remote Similarity	NPD8039	Approved
0.5946	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5141	Approved
0.5921	Remote Similarity	NPD6922	Approved
0.5921	Remote Similarity	NPD6923	Approved
0.5876	Remote Similarity	NPD7128	Approved
0.5876	Remote Similarity	NPD6402	Approved
0.5876	Remote Similarity	NPD4767	Approved
0.5876	Remote Similarity	NPD4768	Approved
0.5876	Remote Similarity	NPD6675	Approved
0.5876	Remote Similarity	NPD5739	Approved
0.5876	Remote Similarity	NPD6008	Approved
0.5851	Remote Similarity	NPD6404	Discontinued
0.5844	Remote Similarity	NPD7143	Approved
0.5844	Remote Similarity	NPD7144	Approved
0.5816	Remote Similarity	NPD5701	Approved
0.5816	Remote Similarity	NPD5697	Approved
0.5816	Remote Similarity	NPD6614	Approved
0.5806	Remote Similarity	NPD3495	Discontinued
0.5806	Remote Similarity	NPD7902	Approved
0.5797	Remote Similarity	NPD4219	Approved
0.5769	Remote Similarity	NPD7150	Approved
0.5769	Remote Similarity	NPD7152	Approved
0.5769	Remote Similarity	NPD7151	Approved
0.5763	Remote Similarity	NPD5783	Phase 3
0.5758	Remote Similarity	NPD4729	Approved
0.5758	Remote Similarity	NPD4730	Approved
0.5758	Remote Similarity	NPD7320	Approved
0.5758	Remote Similarity	NPD5128	Approved
0.5758	Remote Similarity	NPD6899	Approved
0.5758	Remote Similarity	NPD5168	Approved
0.5758	Remote Similarity	NPD6011	Approved
0.5758	Remote Similarity	NPD6881	Approved
0.5714	Remote Similarity	NPD857	Phase 3
0.5714	Remote Similarity	NPD7631	Approved
0.57	Remote Similarity	NPD6012	Approved
0.57	Remote Similarity	NPD6373	Approved
0.57	Remote Similarity	NPD6013	Approved
0.57	Remote Similarity	NPD6014	Approved
0.57	Remote Similarity	NPD6372	Approved
0.5699	Remote Similarity	NPD7614	Phase 1
0.5699	Remote Similarity	NPD7732	Phase 3
0.5692	Remote Similarity	NPD8262	Approved
0.569	Remote Similarity	NPD319	Phase 1
0.5679	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD5785	Approved
0.5657	Remote Similarity	NPD6412	Phase 2
0.5652	Remote Similarity	NPD5282	Discontinued
0.5652	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD5209	Approved
0.5644	Remote Similarity	NPD5250	Approved
0.5644	Remote Similarity	NPD5169	Approved
0.5644	Remote Similarity	NPD5249	Phase 3
0.5644	Remote Similarity	NPD7290	Approved
0.5644	Remote Similarity	NPD6883	Approved
0.5644	Remote Similarity	NPD5248	Approved
0.5644	Remote Similarity	NPD5251	Approved
0.5644	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD7102	Approved
0.5644	Remote Similarity	NPD5247	Approved
0.5644	Remote Similarity	NPD4634	Approved
0.5644	Remote Similarity	NPD5135	Approved
0.5641	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD6939	Phase 2
0.5632	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD5363	Approved
0.5625	Remote Similarity	NPD6926	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