NPASS Compound

Structure

NPC259261 OpenBabel07101718312D 22 23 0 0 1 0 0 0 0 0999 V2000 0.1974 -1.7208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3915 -1.0314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1062 2.9561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6263 -2.0690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9733 0.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2962 1.3663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3004 -1.1716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4344 -0.6716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4855 0.3844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6343 2.3258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6893 1.9987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1538 1.6107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3980 -0.9174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6062 2.0900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2992 -1.1240 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9761 0.2172 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1138 -0.5440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5082 0.8612 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 1.0712 1.2127 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8999 -1.1621 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5037 0.9563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 12 20 1 0 0 0 0 13 19 2 0 0 0 0 15 4 1 6 0 0 0 15 17 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 6 0 0 0 17 21 2 0 0 0 0 18 19 1 0 0 0 0 18 22 2 0 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	344.398
LogP:	3.66
LogD:	3.86
LogS:	-4.569
# Rotatable Bonds:	0
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.464
Synthetic Accessibility Score:	4.677
Fsp3:	0.7
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:	-4.679
MDCK Permeability:	1.5241149412759114e-05
Pgp-inhibitor:	0.965
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.766
30% Bioavailability (F30%):	0.362

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.905
Plasma Protein Binding (PPB):	95.46390533447266%
Volume Distribution (VD):	0.599
Pgp-substrate:	1.9599785804748535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.159
CYP1A2-substrate:	0.446
CYP2C19-inhibitor:	0.444
CYP2C19-substrate:	0.846
CYP2C9-inhibitor:	0.388
CYP2C9-substrate:	0.187
CYP2D6-inhibitor:	0.234
CYP2D6-substrate:	0.273
CYP3A4-inhibitor:	0.597
CYP3A4-substrate:	0.399

ADMET: Excretion

Clearance (CL):	7.14
Half-life (T1/2):	0.707

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.581
Drug-inuced Liver Injury (DILI):	0.302
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.305
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.783
Carcinogencity:	0.67
Eye Corrosion:	0.052
Eye Irritation:	0.269
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC259261

Natural Product ID:	NPC259261
*Common Name:**	7,13-Diketo-1R,8R,11S*-Dolabell-3E,12(18)-Diene
IUPAC Name:	(3aR,5E,10R,12aS)-3a,6,10-trimethyl-1-propan-2-ylidene-3,4,7,8,10,11,12,12a-octahydrocyclopenta[11]annulene-2,9-dione
Synonyms:
Standard InCHIKey:	FFKOVFHESHSZPF-LBVAQWGJSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-13(2)19-16-8-7-15(4)17(21)9-6-14(3)10-11-20(16,5)12-18(19)22/h10,15-16H,6-9,11-12H2,1-5H3/b14-10+/t15-,16-,20-/m1/s1
SMILES:	C/C/1=CC[C@]2(C)CC(=O)C(=C(C)C)[C@H]2CC[C@H](C(=O)CC1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1099119
PubChem CID:	46833123
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001760] Dolabellane and neodolabellane 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
NPO32701	Eunicea	Genus	Plexauridae	Eukaryota	n.a.	southwestern Caribbean	n.a.	PMID[20384296]

☑ 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
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	13200.0	nM	PMID[504074]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Inhibition	<=	50.0	%	PMID[504074]

☑ 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 NPC259261 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	170
0.1-0.2	2549
0.2-0.3	15552
0.3-0.4	11841
0.4-0.5	7436
0.5-0.6	3889
0.6-0.7	1053
0.7-0.8	167
0.8-0.85	20
0.85-0.9	8
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9818	High Similarity	NPC266295
0.9818	High Similarity	NPC94991
0.9474	High Similarity	NPC25853
0.9322	High Similarity	NPC473902
0.9286	High Similarity	NPC267626
0.9286	High Similarity	NPC49575
0.9286	High Similarity	NPC230823
0.9286	High Similarity	NPC55004
0.9123	High Similarity	NPC30215
0.9	High Similarity	NPC212210
0.8983	High Similarity	NPC97322
0.8983	High Similarity	NPC475795
0.8833	High Similarity	NPC165695
0.8833	High Similarity	NPC32285
0.8667	High Similarity	NPC213152
0.8594	High Similarity	NPC139397
0.8571	High Similarity	NPC475523
0.8571	High Similarity	NPC474141
0.8462	Intermediate Similarity	NPC265782
0.8462	Intermediate Similarity	NPC307176
0.8462	Intermediate Similarity	NPC2634
0.8462	Intermediate Similarity	NPC251929
0.8462	Intermediate Similarity	NPC260040
0.8448	Intermediate Similarity	NPC20603
0.8438	Intermediate Similarity	NPC469688
0.8333	Intermediate Similarity	NPC143834
0.8333	Intermediate Similarity	NPC285594
0.8333	Intermediate Similarity	NPC96551
0.8333	Intermediate Similarity	NPC181204
0.8333	Intermediate Similarity	NPC54123
0.8308	Intermediate Similarity	NPC61702
0.8308	Intermediate Similarity	NPC162867
0.8305	Intermediate Similarity	NPC193695
0.8305	Intermediate Similarity	NPC115385
0.8276	Intermediate Similarity	NPC275472
0.8254	Intermediate Similarity	NPC251118
0.8246	Intermediate Similarity	NPC296311
0.8226	Intermediate Similarity	NPC167256
0.8209	Intermediate Similarity	NPC303613
0.8209	Intermediate Similarity	NPC474228
0.8197	Intermediate Similarity	NPC127582
0.8182	Intermediate Similarity	NPC159577
0.8182	Intermediate Similarity	NPC282593
0.8182	Intermediate Similarity	NPC35734
0.8103	Intermediate Similarity	NPC63396
0.8103	Intermediate Similarity	NPC202850
0.8088	Intermediate Similarity	NPC309852
0.8088	Intermediate Similarity	NPC167049
0.8088	Intermediate Similarity	NPC474797
0.8088	Intermediate Similarity	NPC469691
0.8088	Intermediate Similarity	NPC474796
0.8088	Intermediate Similarity	NPC329866
0.8065	Intermediate Similarity	NPC60565
0.806	Intermediate Similarity	NPC115023
0.806	Intermediate Similarity	NPC5701
0.803	Intermediate Similarity	NPC256846
0.803	Intermediate Similarity	NPC469677
0.8	Intermediate Similarity	NPC192427
0.7971	Intermediate Similarity	NPC251435
0.7941	Intermediate Similarity	NPC470044
0.7941	Intermediate Similarity	NPC470045
0.7941	Intermediate Similarity	NPC251705
0.7937	Intermediate Similarity	NPC288253
0.7937	Intermediate Similarity	NPC472306
0.7931	Intermediate Similarity	NPC45283
0.7931	Intermediate Similarity	NPC268564
0.7895	Intermediate Similarity	NPC27438
0.7879	Intermediate Similarity	NPC188292
0.7879	Intermediate Similarity	NPC87141
0.7879	Intermediate Similarity	NPC260474
0.7879	Intermediate Similarity	NPC155198
0.7879	Intermediate Similarity	NPC469679
0.7879	Intermediate Similarity	NPC20610
0.7869	Intermediate Similarity	NPC56905
0.7869	Intermediate Similarity	NPC311852
0.7869	Intermediate Similarity	NPC27610
0.7857	Intermediate Similarity	NPC469796
0.7857	Intermediate Similarity	NPC469646
0.7857	Intermediate Similarity	NPC69408
0.7857	Intermediate Similarity	NPC469793
0.7846	Intermediate Similarity	NPC323005
0.7826	Intermediate Similarity	NPC255021
0.7818	Intermediate Similarity	NPC8610
0.7818	Intermediate Similarity	NPC262558
0.7812	Intermediate Similarity	NPC6697
0.7812	Intermediate Similarity	NPC475124
0.7812	Intermediate Similarity	NPC285371
0.7794	Intermediate Similarity	NPC305501
0.7794	Intermediate Similarity	NPC234707
0.7761	Intermediate Similarity	NPC182815
0.7759	Intermediate Similarity	NPC471751
0.7742	Intermediate Similarity	NPC276764
0.7742	Intermediate Similarity	NPC472304
0.7719	Intermediate Similarity	NPC32351
0.7714	Intermediate Similarity	NPC77501
0.7714	Intermediate Similarity	NPC475771
0.7714	Intermediate Similarity	NPC473171
0.7714	Intermediate Similarity	NPC469669
0.7714	Intermediate Similarity	NPC293803
0.7714	Intermediate Similarity	NPC255650
0.7714	Intermediate Similarity	NPC469678
0.7692	Intermediate Similarity	NPC470329
0.7681	Intermediate Similarity	NPC92909
0.7681	Intermediate Similarity	NPC107783
0.7656	Intermediate Similarity	NPC202118
0.7656	Intermediate Similarity	NPC197238
0.7647	Intermediate Similarity	NPC246722
0.7647	Intermediate Similarity	NPC477856
0.7647	Intermediate Similarity	NPC214770
0.7647	Intermediate Similarity	NPC151045
0.7647	Intermediate Similarity	NPC40574
0.7639	Intermediate Similarity	NPC228911
0.7612	Intermediate Similarity	NPC310992
0.7586	Intermediate Similarity	NPC236623
0.7586	Intermediate Similarity	NPC64866
0.7581	Intermediate Similarity	NPC170799
0.7581	Intermediate Similarity	NPC308108
0.7544	Intermediate Similarity	NPC145311
0.7541	Intermediate Similarity	NPC473733
0.7538	Intermediate Similarity	NPC4638
0.7538	Intermediate Similarity	NPC469662
0.7536	Intermediate Similarity	NPC304983
0.7536	Intermediate Similarity	NPC190035
0.7536	Intermediate Similarity	NPC133253
0.7536	Intermediate Similarity	NPC470078
0.7536	Intermediate Similarity	NPC223187
0.7534	Intermediate Similarity	NPC469690
0.7534	Intermediate Similarity	NPC90965
0.7534	Intermediate Similarity	NPC170793
0.7465	Intermediate Similarity	NPC474011
0.7432	Intermediate Similarity	NPC474509
0.7429	Intermediate Similarity	NPC56747
0.7429	Intermediate Similarity	NPC109576
0.7429	Intermediate Similarity	NPC180015
0.7429	Intermediate Similarity	NPC300940
0.7429	Intermediate Similarity	NPC130016
0.7424	Intermediate Similarity	NPC183422
0.7414	Intermediate Similarity	NPC228776
0.7414	Intermediate Similarity	NPC116906
0.7397	Intermediate Similarity	NPC469996
0.7377	Intermediate Similarity	NPC200258
0.7361	Intermediate Similarity	NPC226242
0.7361	Intermediate Similarity	NPC215481
0.7353	Intermediate Similarity	NPC476614
0.7344	Intermediate Similarity	NPC270042
0.7333	Intermediate Similarity	NPC477372
0.7333	Intermediate Similarity	NPC23117
0.7333	Intermediate Similarity	NPC136150
0.7324	Intermediate Similarity	NPC20025
0.7313	Intermediate Similarity	NPC176171
0.7313	Intermediate Similarity	NPC92327
0.7302	Intermediate Similarity	NPC60772
0.7297	Intermediate Similarity	NPC229204
0.7297	Intermediate Similarity	NPC469620
0.7286	Intermediate Similarity	NPC144627
0.7286	Intermediate Similarity	NPC21944
0.7286	Intermediate Similarity	NPC474562
0.7286	Intermediate Similarity	NPC469737
0.7273	Intermediate Similarity	NPC150162
0.726	Intermediate Similarity	NPC276769
0.726	Intermediate Similarity	NPC91665
0.7246	Intermediate Similarity	NPC286814
0.7246	Intermediate Similarity	NPC477857
0.7237	Intermediate Similarity	NPC469805
0.7237	Intermediate Similarity	NPC469806
0.7237	Intermediate Similarity	NPC193347
0.7237	Intermediate Similarity	NPC3511
0.7237	Intermediate Similarity	NPC469799
0.7237	Intermediate Similarity	NPC20262
0.7237	Intermediate Similarity	NPC320514
0.7237	Intermediate Similarity	NPC256750
0.7237	Intermediate Similarity	NPC469804
0.7237	Intermediate Similarity	NPC472239
0.7237	Intermediate Similarity	NPC142253
0.7231	Intermediate Similarity	NPC260573
0.7222	Intermediate Similarity	NPC476346
0.7222	Intermediate Similarity	NPC65650
0.7222	Intermediate Similarity	NPC469803
0.7222	Intermediate Similarity	NPC216791
0.7213	Intermediate Similarity	NPC95581
0.7206	Intermediate Similarity	NPC4370
0.7206	Intermediate Similarity	NPC176107
0.7206	Intermediate Similarity	NPC290350
0.72	Intermediate Similarity	NPC469797
0.72	Intermediate Similarity	NPC45495
0.72	Intermediate Similarity	NPC469798
0.72	Intermediate Similarity	NPC164218
0.7193	Intermediate Similarity	NPC100380
0.7193	Intermediate Similarity	NPC236355
0.7193	Intermediate Similarity	NPC14917
0.7193	Intermediate Similarity	NPC4079
0.7164	Intermediate Similarity	NPC474329
0.7164	Intermediate Similarity	NPC474304
0.7162	Intermediate Similarity	NPC82635
0.7162	Intermediate Similarity	NPC470052
0.7162	Intermediate Similarity	NPC474056
0.7143	Intermediate Similarity	NPC475622
0.7143	Intermediate Similarity	NPC41539
0.7143	Intermediate Similarity	NPC474976
0.7143	Intermediate Similarity	NPC108045

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 NPC259261 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	2930
0.2-0.3	4326
0.3-0.4	1155
0.4-0.5	288
0.5-0.6	200
0.6-0.7	74
0.7-0.8	7
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8594	High Similarity	NPD4137	Phase 3
0.8462	Intermediate Similarity	NPD4691	Approved
0.8462	Intermediate Similarity	NPD4747	Approved
0.8333	Intermediate Similarity	NPD5276	Approved
0.8088	Intermediate Similarity	NPD4058	Approved
0.8088	Intermediate Similarity	NPD5733	Approved
0.8088	Intermediate Similarity	NPD4687	Approved
0.7879	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD287	Approved
0.7237	Intermediate Similarity	NPD4221	Approved
0.7237	Intermediate Similarity	NPD4223	Phase 3
0.7143	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7331	Phase 2
0.7051	Intermediate Similarity	NPD3133	Approved
0.7051	Intermediate Similarity	NPD4197	Approved
0.7051	Intermediate Similarity	NPD3665	Phase 1
0.7051	Intermediate Similarity	NPD3666	Approved
0.6962	Remote Similarity	NPD5329	Approved
0.6933	Remote Similarity	NPD3617	Approved
0.6933	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3618	Phase 1
0.6875	Remote Similarity	NPD7146	Approved
0.6875	Remote Similarity	NPD5280	Approved
0.6875	Remote Similarity	NPD5279	Phase 3
0.6875	Remote Similarity	NPD4688	Approved
0.6875	Remote Similarity	NPD5690	Phase 2
0.6875	Remote Similarity	NPD5205	Approved
0.6875	Remote Similarity	NPD5330	Approved
0.6875	Remote Similarity	NPD6684	Approved
0.6875	Remote Similarity	NPD4693	Phase 3
0.6875	Remote Similarity	NPD4138	Approved
0.6875	Remote Similarity	NPD4689	Approved
0.6875	Remote Similarity	NPD4694	Approved
0.6875	Remote Similarity	NPD6409	Approved
0.6875	Remote Similarity	NPD4690	Approved
0.6875	Remote Similarity	NPD7334	Approved
0.6875	Remote Similarity	NPD7521	Approved
0.6795	Remote Similarity	NPD3667	Approved
0.6753	Remote Similarity	NPD4695	Discontinued
0.6707	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6903	Approved
0.6707	Remote Similarity	NPD5737	Approved
0.6707	Remote Similarity	NPD4518	Approved
0.6707	Remote Similarity	NPD5208	Approved
0.6707	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD7341	Phase 2
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5328	Approved
0.6627	Remote Similarity	NPD6904	Approved
0.6627	Remote Similarity	NPD6673	Approved
0.6627	Remote Similarity	NPD4753	Phase 2
0.6627	Remote Similarity	NPD6080	Approved
0.6625	Remote Similarity	NPD4786	Approved
0.6625	Remote Similarity	NPD3668	Phase 3
0.661	Remote Similarity	NPD344	Approved
0.661	Remote Similarity	NPD343	Approved
0.661	Remote Similarity	NPD345	Approved
0.6548	Remote Similarity	NPD4096	Approved
0.6548	Remote Similarity	NPD5692	Phase 3
0.6548	Remote Similarity	NPD5207	Approved
0.6471	Remote Similarity	NPD5693	Phase 1
0.6471	Remote Similarity	NPD5281	Approved
0.6471	Remote Similarity	NPD6050	Approved
0.6471	Remote Similarity	NPD6079	Approved
0.6471	Remote Similarity	NPD5694	Approved
0.6471	Remote Similarity	NPD5284	Approved
0.6463	Remote Similarity	NPD4623	Approved
0.6463	Remote Similarity	NPD6098	Approved
0.6463	Remote Similarity	NPD4519	Discontinued
0.6456	Remote Similarity	NPD8028	Phase 2
0.641	Remote Similarity	NPD4195	Approved
0.6395	Remote Similarity	NPD4202	Approved
0.6375	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD5785	Approved
0.6341	Remote Similarity	NPD5363	Approved
0.6329	Remote Similarity	NPD5368	Approved
0.6322	Remote Similarity	NPD6001	Approved
0.6308	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5210	Approved
0.625	Remote Similarity	NPD5783	Phase 3
0.625	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD4692	Approved
0.625	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5369	Approved
0.625	Remote Similarity	NPD4139	Approved
0.625	Remote Similarity	NPD4629	Approved
0.6232	Remote Similarity	NPD4193	Approved
0.6232	Remote Similarity	NPD4192	Approved
0.6232	Remote Similarity	NPD4191	Approved
0.6232	Remote Similarity	NPD4194	Approved
0.6207	Remote Similarity	NPD5133	Approved
0.619	Remote Similarity	NPD3573	Approved
0.618	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4697	Phase 3
0.618	Remote Similarity	NPD5221	Approved
0.618	Remote Similarity	NPD5222	Approved
0.6173	Remote Similarity	NPD6435	Approved
0.6173	Remote Similarity	NPD5209	Approved
0.6173	Remote Similarity	NPD4270	Approved
0.6173	Remote Similarity	NPD4269	Approved
0.6145	Remote Similarity	NPD1694	Approved
0.6143	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD4252	Approved
0.6111	Remote Similarity	NPD6083	Phase 2
0.6111	Remote Similarity	NPD5173	Approved
0.6111	Remote Similarity	NPD6084	Phase 2
0.6111	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4755	Approved
0.6098	Remote Similarity	NPD4788	Approved
0.6098	Remote Similarity	NPD5362	Discontinued
0.6067	Remote Similarity	NPD5654	Approved
0.6044	Remote Similarity	NPD5696	Approved
0.6023	Remote Similarity	NPD6399	Phase 3
0.5978	Remote Similarity	NPD4700	Approved
0.5978	Remote Similarity	NPD4696	Approved
0.5978	Remote Similarity	NPD5286	Approved
0.5978	Remote Similarity	NPD5285	Approved
0.5955	Remote Similarity	NPD5282	Discontinued
0.5938	Remote Similarity	NPD28	Approved
0.5938	Remote Similarity	NPD29	Approved
0.5934	Remote Similarity	NPD5959	Approved
0.5914	Remote Similarity	NPD5223	Approved
0.5909	Remote Similarity	NPD7515	Phase 2
0.5897	Remote Similarity	NPD8039	Approved
0.5882	Remote Similarity	NPD5786	Approved
0.5867	Remote Similarity	NPD6923	Approved
0.5867	Remote Similarity	NPD6922	Approved
0.5862	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD857	Phase 3
0.5851	Remote Similarity	NPD5226	Approved
0.5851	Remote Similarity	NPD5211	Phase 2
0.5851	Remote Similarity	NPD5091	Approved
0.5851	Remote Similarity	NPD4633	Approved
0.5851	Remote Similarity	NPD5225	Approved
0.5851	Remote Similarity	NPD5224	Approved
0.5789	Remote Similarity	NPD5175	Approved
0.5789	Remote Similarity	NPD7143	Approved
0.5789	Remote Similarity	NPD4754	Approved
0.5789	Remote Similarity	NPD6052	Approved
0.5789	Remote Similarity	NPD7144	Approved
0.5789	Remote Similarity	NPD5174	Approved
0.5783	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD7748	Approved
0.5778	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD7900	Approved
0.5769	Remote Similarity	NPD6926	Approved
0.5769	Remote Similarity	NPD6924	Approved
0.5758	Remote Similarity	NPD3172	Approved
0.5753	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD4822	Approved
0.5732	Remote Similarity	NPD4819	Approved
0.5732	Remote Similarity	NPD4821	Approved
0.5732	Remote Similarity	NPD4820	Approved
0.5729	Remote Similarity	NPD5141	Approved
0.5714	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5331	Approved
0.5714	Remote Similarity	NPD4243	Approved
0.5714	Remote Similarity	NPD7151	Approved
0.5714	Remote Similarity	NPD7154	Phase 3
0.5714	Remote Similarity	NPD5332	Approved
0.5714	Remote Similarity	NPD7150	Approved
0.5714	Remote Similarity	NPD7152	Approved
0.5679	Remote Similarity	NPD4271	Approved
0.5679	Remote Similarity	NPD4268	Approved
0.5672	Remote Similarity	NPD3196	Approved
0.5672	Remote Similarity	NPD3195	Phase 2
0.5672	Remote Similarity	NPD3194	Approved
0.5672	Remote Similarity	NPD4266	Approved
0.567	Remote Similarity	NPD7128	Approved
0.567	Remote Similarity	NPD6675	Approved
0.567	Remote Similarity	NPD4768	Approved
0.567	Remote Similarity	NPD4767	Approved
0.567	Remote Similarity	NPD6008	Approved
0.567	Remote Similarity	NPD5739	Approved
0.567	Remote Similarity	NPD6402	Approved
0.5663	Remote Similarity	NPD4790	Discontinued
0.5645	Remote Similarity	NPD3174	Discontinued
0.5638	Remote Similarity	NPD6404	Discontinued
0.5625	Remote Similarity	NPD6933	Approved
0.5625	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5616	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD5697	Approved
0.5612	Remote Similarity	NPD5701	Approved
0.5612	Remote Similarity	NPD6412	Phase 2
0.5612	Remote Similarity	NPD6614	Approved
0.5604	Remote Similarity	NPD5769	Clinical (unspecified phase)

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