NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	218.17
Volume:	245.844
LogP:	4.26
LogD:	4.381
LogS:	-5.191
# Rotatable Bonds:	0
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.605
Synthetic Accessibility Score:	5.336
Fsp3:	0.8
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:	-4.722
MDCK Permeability:	2.2177249775268137e-05
Pgp-inhibitor:	0.093
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.062

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.195
Plasma Protein Binding (PPB):	93.61356353759766%
Volume Distribution (VD):	0.761
Pgp-substrate:	9.812101364135742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.157
CYP1A2-substrate:	0.605
CYP2C19-inhibitor:	0.8
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.517
CYP2C9-substrate:	0.757
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.586
CYP3A4-inhibitor:	0.176
CYP3A4-substrate:	0.417

ADMET: Excretion

Clearance (CL):	14.179
Half-life (T1/2):	0.139

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.203
Drug-inuced Liver Injury (DILI):	0.158
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.254
Skin Sensitization:	0.135
Carcinogencity:	0.196
Eye Corrosion:	0.037
Eye Irritation:	0.368
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: NPC472306

Natural Product ID:	NPC472306
*Common Name:**	GIGKXOAUYMWORB-IWPPJYEWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GIGKXOAUYMWORB-IWPPJYEWSA-N
Standard InCHI:	InChI=1S/C15H22O/c1-9-5-6-11-7-12-10(2)13(16)8-15(9,12)14(11,3)4/h9,11H,5-8H2,1-4H3/t9-,11?,15?/m1/s1
SMILES:	CC1CCC2CC3=C(C(=O)CC13C2(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3358077
PubChem CID:	n.a.
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
NPO32931	pterolobium macropterum	Species	Fabaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[25337628]

☑ 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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	138280.0	nM	PMID[456634]

☑ 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 NPC472306 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	175
0.1-0.2	3340
0.2-0.3	17241
0.3-0.4	9916
0.4-0.5	7730
0.5-0.6	3339
0.6-0.7	816
0.7-0.8	124
0.8-0.85	15
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8689	High Similarity	NPC270042
0.8548	High Similarity	NPC213152
0.8413	Intermediate Similarity	NPC165695
0.8358	Intermediate Similarity	NPC159577
0.8358	Intermediate Similarity	NPC35734
0.8358	Intermediate Similarity	NPC307176
0.8358	Intermediate Similarity	NPC282593
0.8281	Intermediate Similarity	NPC212210
0.8235	Intermediate Similarity	NPC115023
0.8235	Intermediate Similarity	NPC223187
0.8209	Intermediate Similarity	NPC139397
0.8197	Intermediate Similarity	NPC192427
0.8197	Intermediate Similarity	NPC115385
0.8116	Intermediate Similarity	NPC251705
0.8116	Intermediate Similarity	NPC470044
0.8116	Intermediate Similarity	NPC303613
0.8116	Intermediate Similarity	NPC470045
0.8116	Intermediate Similarity	NPC474228
0.8095	Intermediate Similarity	NPC127582
0.8095	Intermediate Similarity	NPC25853
0.8088	Intermediate Similarity	NPC2634
0.8088	Intermediate Similarity	NPC260040
0.8088	Intermediate Similarity	NPC265782
0.8088	Intermediate Similarity	NPC251929
0.8065	Intermediate Similarity	NPC56905
0.8065	Intermediate Similarity	NPC27610
0.8065	Intermediate Similarity	NPC94991
0.8065	Intermediate Similarity	NPC266295
0.806	Intermediate Similarity	NPC20610
0.8	Intermediate Similarity	NPC285371
0.8	Intermediate Similarity	NPC255021
0.8	Intermediate Similarity	NPC475124
0.7971	Intermediate Similarity	NPC234707
0.7971	Intermediate Similarity	NPC305501
0.7971	Intermediate Similarity	NPC54123
0.7971	Intermediate Similarity	NPC5701
0.7941	Intermediate Similarity	NPC182815
0.7937	Intermediate Similarity	NPC472304
0.7937	Intermediate Similarity	NPC259261
0.7937	Intermediate Similarity	NPC276764
0.791	Intermediate Similarity	NPC475523
0.7903	Intermediate Similarity	NPC267626
0.7903	Intermediate Similarity	NPC49575
0.7903	Intermediate Similarity	NPC55004
0.7887	Intermediate Similarity	NPC293803
0.7826	Intermediate Similarity	NPC246722
0.7826	Intermediate Similarity	NPC477856
0.7826	Intermediate Similarity	NPC151045
0.7826	Intermediate Similarity	NPC214770
0.7808	Intermediate Similarity	NPC228911
0.7797	Intermediate Similarity	NPC274182
0.7778	Intermediate Similarity	NPC69408
0.7778	Intermediate Similarity	NPC30215
0.7761	Intermediate Similarity	NPC176171
0.7761	Intermediate Similarity	NPC323005
0.7746	Intermediate Similarity	NPC474796
0.7746	Intermediate Similarity	NPC474797
0.7746	Intermediate Similarity	NPC329866
0.7746	Intermediate Similarity	NPC309852
0.7742	Intermediate Similarity	NPC20603
0.7727	Intermediate Similarity	NPC473902
0.7727	Intermediate Similarity	NPC6697
0.7714	Intermediate Similarity	NPC470078
0.7692	Intermediate Similarity	NPC60565
0.7681	Intermediate Similarity	NPC256846
0.7639	Intermediate Similarity	NPC255650
0.7639	Intermediate Similarity	NPC473171
0.7639	Intermediate Similarity	NPC469803
0.7627	Intermediate Similarity	NPC116906
0.7619	Intermediate Similarity	NPC230823
0.7581	Intermediate Similarity	NPC200258
0.7576	Intermediate Similarity	NPC32285
0.7571	Intermediate Similarity	NPC40574
0.7568	Intermediate Similarity	NPC469996
0.7541	Intermediate Similarity	NPC474141
0.7536	Intermediate Similarity	NPC260474
0.7536	Intermediate Similarity	NPC188292
0.7536	Intermediate Similarity	NPC310992
0.7534	Intermediate Similarity	NPC469796
0.7534	Intermediate Similarity	NPC469793
0.75	Intermediate Similarity	NPC236623
0.75	Intermediate Similarity	NPC39462
0.75	Intermediate Similarity	NPC96812
0.75	Intermediate Similarity	NPC170799
0.75	Intermediate Similarity	NPC308108
0.75	Intermediate Similarity	NPC92327
0.75	Intermediate Similarity	NPC107704
0.75	Intermediate Similarity	NPC43300
0.75	Intermediate Similarity	NPC168824
0.75	Intermediate Similarity	NPC189917
0.7467	Intermediate Similarity	NPC170793
0.7467	Intermediate Similarity	NPC90965
0.7465	Intermediate Similarity	NPC304983
0.7463	Intermediate Similarity	NPC469662
0.7458	Intermediate Similarity	NPC293343
0.7458	Intermediate Similarity	NPC247786
0.7458	Intermediate Similarity	NPC258672
0.7429	Intermediate Similarity	NPC477857
0.7424	Intermediate Similarity	NPC97322
0.7424	Intermediate Similarity	NPC475795
0.7414	Intermediate Similarity	NPC14917
0.7414	Intermediate Similarity	NPC236355
0.7414	Intermediate Similarity	NPC4079
0.7391	Intermediate Similarity	NPC176107
0.7385	Intermediate Similarity	NPC143834
0.7368	Intermediate Similarity	NPC474509
0.7361	Intermediate Similarity	NPC52667
0.7353	Intermediate Similarity	NPC251118
0.7333	Intermediate Similarity	NPC23778
0.7313	Intermediate Similarity	NPC202118
0.7313	Intermediate Similarity	NPC197238
0.7313	Intermediate Similarity	NPC167256
0.7313	Intermediate Similarity	NPC288253
0.7288	Intermediate Similarity	NPC294440
0.7286	Intermediate Similarity	NPC155198
0.7286	Intermediate Similarity	NPC87141
0.7273	Intermediate Similarity	NPC477372
0.7258	Intermediate Similarity	NPC268564
0.7231	Intermediate Similarity	NPC311852
0.7222	Intermediate Similarity	NPC190035
0.7222	Intermediate Similarity	NPC144627
0.7222	Intermediate Similarity	NPC181204
0.7222	Intermediate Similarity	NPC474562
0.72	Intermediate Similarity	NPC91665
0.7183	Intermediate Similarity	NPC61702
0.7183	Intermediate Similarity	NPC162867
0.7179	Intermediate Similarity	NPC472867
0.7179	Intermediate Similarity	NPC320514
0.7179	Intermediate Similarity	NPC142253
0.7179	Intermediate Similarity	NPC321289
0.7179	Intermediate Similarity	NPC472239
0.7179	Intermediate Similarity	NPC193347
0.7179	Intermediate Similarity	NPC327969
0.7179	Intermediate Similarity	NPC3511
0.7143	Intermediate Similarity	NPC469797
0.7143	Intermediate Similarity	NPC469798
0.7143	Intermediate Similarity	NPC220210
0.7143	Intermediate Similarity	NPC20181
0.7143	Intermediate Similarity	NPC250539
0.7143	Intermediate Similarity	NPC290350
0.7143	Intermediate Similarity	NPC4370
0.7123	Intermediate Similarity	NPC56747
0.7123	Intermediate Similarity	NPC109576
0.7123	Intermediate Similarity	NPC180015
0.7123	Intermediate Similarity	NPC130016
0.7121	Intermediate Similarity	NPC285594
0.7121	Intermediate Similarity	NPC96551
0.7119	Intermediate Similarity	NPC131981
0.7119	Intermediate Similarity	NPC40249
0.7119	Intermediate Similarity	NPC173996
0.7105	Intermediate Similarity	NPC82635
0.7105	Intermediate Similarity	NPC470052
0.7101	Intermediate Similarity	NPC470329
0.7089	Intermediate Similarity	NPC470015
0.7089	Intermediate Similarity	NPC271784
0.7089	Intermediate Similarity	NPC41539
0.7089	Intermediate Similarity	NPC168188
0.7089	Intermediate Similarity	NPC469561
0.7042	Intermediate Similarity	NPC296697
0.7042	Intermediate Similarity	NPC39157
0.7042	Intermediate Similarity	NPC142754
0.7042	Intermediate Similarity	NPC82477
0.7031	Intermediate Similarity	NPC184819
0.7027	Intermediate Similarity	NPC159497
0.7013	Intermediate Similarity	NPC477371
0.7013	Intermediate Similarity	NPC472490
0.7013	Intermediate Similarity	NPC215843
0.7	Intermediate Similarity	NPC87552
0.7	Intermediate Similarity	NPC320801
0.7	Intermediate Similarity	NPC144258
0.7	Intermediate Similarity	NPC16287
0.7	Intermediate Similarity	NPC237712
0.7	Intermediate Similarity	NPC214043
0.7	Intermediate Similarity	NPC178025
0.7	Intermediate Similarity	NPC473246
0.7	Intermediate Similarity	NPC181743
0.7	Intermediate Similarity	NPC85774
0.7	Intermediate Similarity	NPC475100
0.7	Intermediate Similarity	NPC209882
0.6986	Remote Similarity	NPC21944
0.6986	Remote Similarity	NPC133253
0.6986	Remote Similarity	NPC225467
0.6984	Remote Similarity	NPC296311
0.6984	Remote Similarity	NPC23117
0.6974	Remote Similarity	NPC470557
0.6974	Remote Similarity	NPC74685
0.6974	Remote Similarity	NPC475932
0.697	Remote Similarity	NPC60772
0.6962	Remote Similarity	NPC469805
0.6962	Remote Similarity	NPC469806
0.6962	Remote Similarity	NPC469799
0.6962	Remote Similarity	NPC100297
0.6962	Remote Similarity	NPC469325
0.6962	Remote Similarity	NPC469804
0.6944	Remote Similarity	NPC286814
0.6935	Remote Similarity	NPC64866
0.6933	Remote Similarity	NPC65650
0.6933	Remote Similarity	NPC476346
0.6923	Remote Similarity	NPC472478
0.6923	Remote Similarity	NPC279667

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 NPC472306 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	3317
0.2-0.3	4255
0.3-0.4	892
0.4-0.5	243
0.5-0.6	182
0.6-0.7	76
0.7-0.8	6
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8358	Intermediate Similarity	NPD4747	Approved
0.8209	Intermediate Similarity	NPD4137	Phase 3
0.8088	Intermediate Similarity	NPD4691	Approved
0.8	Intermediate Similarity	NPD4687	Approved
0.8	Intermediate Similarity	NPD5733	Approved
0.7971	Intermediate Similarity	NPD5276	Approved
0.7794	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD4058	Approved
0.75	Intermediate Similarity	NPD287	Approved
0.7333	Intermediate Similarity	NPD3617	Approved
0.7179	Intermediate Similarity	NPD4223	Phase 3
0.7179	Intermediate Similarity	NPD4221	Approved
0.7119	Intermediate Similarity	NPD344	Approved
0.7119	Intermediate Similarity	NPD345	Approved
0.7119	Intermediate Similarity	NPD343	Approved
0.7	Intermediate Similarity	NPD4197	Approved
0.6914	Remote Similarity	NPD5329	Approved
0.6875	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4139	Approved
0.6835	Remote Similarity	NPD4692	Approved
0.6829	Remote Similarity	NPD4688	Approved
0.6829	Remote Similarity	NPD4689	Approved
0.6829	Remote Similarity	NPD5690	Phase 2
0.6829	Remote Similarity	NPD5205	Approved
0.6829	Remote Similarity	NPD4693	Phase 3
0.6829	Remote Similarity	NPD4138	Approved
0.6829	Remote Similarity	NPD5280	Approved
0.6829	Remote Similarity	NPD4694	Approved
0.6829	Remote Similarity	NPD4690	Approved
0.679	Remote Similarity	NPD3133	Approved
0.679	Remote Similarity	NPD3665	Phase 1
0.679	Remote Similarity	NPD3666	Approved
0.6706	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6627	Remote Similarity	NPD7521	Approved
0.6627	Remote Similarity	NPD3618	Phase 1
0.6627	Remote Similarity	NPD7334	Approved
0.6627	Remote Similarity	NPD6409	Approved
0.6627	Remote Similarity	NPD7146	Approved
0.6627	Remote Similarity	NPD5279	Phase 3
0.6627	Remote Similarity	NPD6684	Approved
0.6627	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5330	Approved
0.6588	Remote Similarity	NPD6904	Approved
0.6588	Remote Similarity	NPD6080	Approved
0.6588	Remote Similarity	NPD4753	Phase 2
0.6588	Remote Similarity	NPD5328	Approved
0.6588	Remote Similarity	NPD6673	Approved
0.6585	Remote Similarity	NPD4786	Approved
0.6543	Remote Similarity	NPD3667	Approved
0.6512	Remote Similarity	NPD5692	Phase 3
0.6477	Remote Similarity	NPD6001	Approved
0.6471	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6079	Approved
0.6437	Remote Similarity	NPD5694	Approved
0.6437	Remote Similarity	NPD5284	Approved
0.6437	Remote Similarity	NPD5693	Phase 1
0.6437	Remote Similarity	NPD5281	Approved
0.6437	Remote Similarity	NPD6050	Approved
0.6429	Remote Similarity	NPD6098	Approved
0.6429	Remote Similarity	NPD4519	Discontinued
0.6429	Remote Similarity	NPD4623	Approved
0.642	Remote Similarity	NPD8028	Phase 2
0.6404	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD3668	Phase 3
0.6375	Remote Similarity	NPD4195	Approved
0.6364	Remote Similarity	NPD5133	Approved
0.6364	Remote Similarity	NPD4202	Approved
0.6322	Remote Similarity	NPD4096	Approved
0.6296	Remote Similarity	NPD4695	Discontinued
0.6265	Remote Similarity	NPD4788	Approved
0.6222	Remote Similarity	NPD5654	Approved
0.6222	Remote Similarity	NPD4629	Approved
0.6222	Remote Similarity	NPD5210	Approved
0.6222	Remote Similarity	NPD5695	Phase 3
0.6164	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD7341	Phase 2
0.6154	Remote Similarity	NPD5222	Approved
0.6154	Remote Similarity	NPD5221	Approved
0.6154	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4697	Phase 3
0.6092	Remote Similarity	NPD4518	Approved
0.6087	Remote Similarity	NPD4755	Approved
0.6087	Remote Similarity	NPD6084	Phase 2
0.6087	Remote Similarity	NPD5173	Approved
0.6087	Remote Similarity	NPD6083	Phase 2
0.6087	Remote Similarity	NPD5959	Approved
0.6022	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD6399	Phase 3
0.5977	Remote Similarity	NPD3573	Approved
0.5957	Remote Similarity	NPD5286	Approved
0.5957	Remote Similarity	NPD5285	Approved
0.5957	Remote Similarity	NPD4700	Approved
0.5957	Remote Similarity	NPD4696	Approved
0.5952	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6052	Approved
0.593	Remote Similarity	NPD1694	Approved
0.5921	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD5360	Phase 3
0.5897	Remote Similarity	NPD4243	Approved
0.5895	Remote Similarity	NPD5223	Approved
0.5867	Remote Similarity	NPD7331	Phase 2
0.5867	Remote Similarity	NPD4224	Phase 2
0.5854	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5226	Approved
0.5833	Remote Similarity	NPD5211	Phase 2
0.5833	Remote Similarity	NPD5225	Approved
0.5833	Remote Similarity	NPD5224	Approved
0.5833	Remote Similarity	NPD4633	Approved
0.5833	Remote Similarity	NPD5091	Approved
0.5816	Remote Similarity	NPD6008	Approved
0.5797	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD5174	Approved
0.5773	Remote Similarity	NPD4754	Approved
0.5773	Remote Similarity	NPD5175	Approved
0.5769	Remote Similarity	NPD4789	Approved
0.5761	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.575	Remote Similarity	NPD4784	Approved
0.575	Remote Similarity	NPD4785	Approved
0.5747	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD1696	Phase 3
0.5714	Remote Similarity	NPD5141	Approved
0.5714	Remote Similarity	NPD7515	Phase 2
0.57	Remote Similarity	NPD7320	Approved
0.5696	Remote Similarity	NPD6081	Approved
0.5696	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD4758	Discontinued
0.5696	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD5275	Approved
0.5679	Remote Similarity	NPD4190	Phase 3
0.5679	Remote Similarity	NPD7339	Approved
0.5679	Remote Similarity	NPD6942	Approved
0.5657	Remote Similarity	NPD4768	Approved
0.5657	Remote Similarity	NPD7128	Approved
0.5657	Remote Similarity	NPD4767	Approved
0.5657	Remote Similarity	NPD6675	Approved
0.5657	Remote Similarity	NPD5739	Approved
0.5657	Remote Similarity	NPD6402	Approved
0.5645	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD6922	Approved
0.5641	Remote Similarity	NPD3698	Phase 2
0.5641	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD6923	Approved
0.5625	Remote Similarity	NPD6404	Discontinued
0.56	Remote Similarity	NPD5697	Approved
0.56	Remote Similarity	NPD6614	Approved
0.56	Remote Similarity	NPD5701	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