NPASS Compound

Structure

NPC25853 OpenBabel07101718292D 21 22 0 0 1 0 0 0 0 0999 V2000 2.4627 2.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8737 2.9334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0350 -1.7434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5551 3.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9021 0.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4143 0.8283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2251 -0.1536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0426 1.7567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5632 -1.1131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5794 0.3515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6182 -0.7861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9174 -0.3980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3632 1.8843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4692 2.1301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5350 -0.8774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2281 2.3367 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 0.0951 0.9955 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2292 2.3843 0.0000 C 0 0 0 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 -0.9934 3.3561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 10 12 1 0 0 0 0 10 17 1 0 0 0 0 11 20 1 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 16 19 1 0 0 0 0 17 14 1 6 0 0 0 17 18 1 0 0 0 0 18 20 1 1 0 0 0 19 21 2 0 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.23
Volume:	335.608
LogP:	4.872
LogD:	4.662
LogS:	-5.214
# 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:	0.583
Synthetic Accessibility Score:	4.918
Fsp3:	0.65
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:	-4.603
MDCK Permeability:	1.5988100130925886e-05
Pgp-inhibitor:	0.541
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.049
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.609
Plasma Protein Binding (PPB):	96.68822479248047%
Volume Distribution (VD):	2.203
Pgp-substrate:	3.605128765106201%

ADMET: Metabolism

CYP1A2-inhibitor:	0.429
CYP1A2-substrate:	0.624
CYP2C19-inhibitor:	0.354
CYP2C19-substrate:	0.789
CYP2C9-inhibitor:	0.335
CYP2C9-substrate:	0.392
CYP2D6-inhibitor:	0.225
CYP2D6-substrate:	0.821
CYP3A4-inhibitor:	0.865
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	7.143
Half-life (T1/2):	0.32

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.144
Drug-inuced Liver Injury (DILI):	0.441
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.127
Skin Sensitization:	0.478
Carcinogencity:	0.092
Eye Corrosion:	0.945
Eye Irritation:	0.907
Respiratory Toxicity:	0.266

Download Data

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

Natural Product: NPC25853

Natural Product ID:	NPC25853
*Common Name:**	(1R,3E,7E,11S,12R)-Dolabella-3,7,18-Trien-9-One
IUPAC Name:	(1R,3aR,5E,9E,12aS)-3a,6,10-trimethyl-1-prop-1-en-2-yl-1,2,3,4,7,8,12,12a-octahydrocyclopenta[11]annulen-11-one
Synonyms:
Standard InCHIKey:	QWFVFRAHUCTMJX-SJGBTTITSA-N
Standard InCHI:	InChI=1S/C20H30O/c1-14(2)17-10-12-20(5)11-9-15(3)7-6-8-16(4)19(21)13-18(17)20/h8-9,17-18H,1,6-7,10-13H2,2-5H3/b15-9+,16-8+/t17-,18-,20-/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@]2(C)C/C=C(C)/CC/C=C(C)/C(=O)C[C@@H]12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1270047
PubChem CID:	49831551
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
NPO23505	Convexella magelhaenica	Species	Primnoidae	Eukaryota	n.a.	South Atlantic	n.a.	PMID[20853878]
NPO23505	Convexella magelhaenica	Species	Primnoidae	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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	39800.0	nM	PMID[450163]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2500.0	nM	PMID[450163]

☑ 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 NPC25853 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	213
0.1-0.2	3001
0.2-0.3	16199
0.3-0.4	11509
0.4-0.5	7067
0.5-0.6	3624
0.6-0.7	891
0.7-0.8	150
0.8-0.85	22
0.85-0.9	5
0.9-0.95	12
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC94991
0.9643	High Similarity	NPC30215
0.9643	High Similarity	NPC266295
0.9474	High Similarity	NPC259261
0.9464	High Similarity	NPC267626
0.9464	High Similarity	NPC49575
0.9464	High Similarity	NPC55004
0.9322	High Similarity	NPC165695
0.9167	High Similarity	NPC473902
0.9153	High Similarity	NPC475795
0.9123	High Similarity	NPC230823
0.8852	High Similarity	NPC212210
0.8833	High Similarity	NPC97322
0.8833	High Similarity	NPC213152
0.8689	High Similarity	NPC32285
0.85	High Similarity	NPC285594
0.85	High Similarity	NPC96551
0.85	High Similarity	NPC143834
0.8462	Intermediate Similarity	NPC61702
0.8462	Intermediate Similarity	NPC162867
0.8438	Intermediate Similarity	NPC475523
0.8387	Intermediate Similarity	NPC167256
0.8358	Intermediate Similarity	NPC251705
0.8358	Intermediate Similarity	NPC303613
0.8358	Intermediate Similarity	NPC470044
0.8358	Intermediate Similarity	NPC474228
0.8358	Intermediate Similarity	NPC470045
0.8333	Intermediate Similarity	NPC251929
0.8333	Intermediate Similarity	NPC159577
0.8333	Intermediate Similarity	NPC307176
0.8333	Intermediate Similarity	NPC35734
0.8333	Intermediate Similarity	NPC265782
0.8333	Intermediate Similarity	NPC2634
0.8333	Intermediate Similarity	NPC282593
0.8305	Intermediate Similarity	NPC20603
0.8235	Intermediate Similarity	NPC309852
0.8209	Intermediate Similarity	NPC54123
0.8209	Intermediate Similarity	NPC234707
0.8209	Intermediate Similarity	NPC5701
0.8209	Intermediate Similarity	NPC115023
0.8182	Intermediate Similarity	NPC139397
0.8167	Intermediate Similarity	NPC115385
0.8125	Intermediate Similarity	NPC251118
0.8116	Intermediate Similarity	NPC293803
0.8116	Intermediate Similarity	NPC251435
0.8103	Intermediate Similarity	NPC296311
0.8103	Intermediate Similarity	NPC474141
0.8095	Intermediate Similarity	NPC472306
0.8065	Intermediate Similarity	NPC127582
0.806	Intermediate Similarity	NPC260040
0.803	Intermediate Similarity	NPC469688
0.803	Intermediate Similarity	NPC20610
0.8	Intermediate Similarity	NPC69408
0.7971	Intermediate Similarity	NPC474797
0.7971	Intermediate Similarity	NPC329866
0.7971	Intermediate Similarity	NPC255021
0.7971	Intermediate Similarity	NPC474796
0.7941	Intermediate Similarity	NPC181204
0.7941	Intermediate Similarity	NPC305501
0.791	Intermediate Similarity	NPC256846
0.791	Intermediate Similarity	NPC469677
0.791	Intermediate Similarity	NPC182815
0.7869	Intermediate Similarity	NPC193695
0.7857	Intermediate Similarity	NPC255650
0.7833	Intermediate Similarity	NPC275472
0.7812	Intermediate Similarity	NPC288253
0.7797	Intermediate Similarity	NPC268564
0.7794	Intermediate Similarity	NPC477856
0.7794	Intermediate Similarity	NPC214770
0.7778	Intermediate Similarity	NPC228911
0.7778	Intermediate Similarity	NPC270042
0.7761	Intermediate Similarity	NPC87141
0.7761	Intermediate Similarity	NPC155198
0.7761	Intermediate Similarity	NPC469679
0.7761	Intermediate Similarity	NPC310992
0.7761	Intermediate Similarity	NPC188292
0.7761	Intermediate Similarity	NPC260474
0.7759	Intermediate Similarity	NPC27438
0.7746	Intermediate Similarity	NPC469793
0.7746	Intermediate Similarity	NPC469796
0.7742	Intermediate Similarity	NPC27610
0.7742	Intermediate Similarity	NPC56905
0.7742	Intermediate Similarity	NPC311852
0.7727	Intermediate Similarity	NPC323005
0.7727	Intermediate Similarity	NPC92327
0.7727	Intermediate Similarity	NPC176171
0.7719	Intermediate Similarity	NPC145311
0.7714	Intermediate Similarity	NPC167049
0.7714	Intermediate Similarity	NPC469691
0.7692	Intermediate Similarity	NPC475124
0.7692	Intermediate Similarity	NPC285371
0.7692	Intermediate Similarity	NPC6697
0.7681	Intermediate Similarity	NPC304983
0.7681	Intermediate Similarity	NPC470078
0.7671	Intermediate Similarity	NPC170793
0.7671	Intermediate Similarity	NPC90965
0.7667	Intermediate Similarity	NPC202850
0.7667	Intermediate Similarity	NPC63396
0.7656	Intermediate Similarity	NPC60565
0.7627	Intermediate Similarity	NPC471751
0.7619	Intermediate Similarity	NPC472304
0.7619	Intermediate Similarity	NPC276764
0.7612	Intermediate Similarity	NPC176107
0.7606	Intermediate Similarity	NPC469678
0.7606	Intermediate Similarity	NPC77501
0.7606	Intermediate Similarity	NPC469669
0.7606	Intermediate Similarity	NPC475771
0.7586	Intermediate Similarity	NPC32351
0.7581	Intermediate Similarity	NPC192427
0.7576	Intermediate Similarity	NPC183422
0.7576	Intermediate Similarity	NPC470329
0.7571	Intermediate Similarity	NPC92909
0.7571	Intermediate Similarity	NPC107783
0.7568	Intermediate Similarity	NPC474509
0.7538	Intermediate Similarity	NPC202118
0.7538	Intermediate Similarity	NPC197238
0.7536	Intermediate Similarity	NPC40574
0.7536	Intermediate Similarity	NPC246722
0.7536	Intermediate Similarity	NPC151045
0.75	Intermediate Similarity	NPC469646
0.75	Intermediate Similarity	NPC215481
0.75	Intermediate Similarity	NPC23117
0.75	Intermediate Similarity	NPC45283
0.746	Intermediate Similarity	NPC308108
0.746	Intermediate Similarity	NPC170799
0.746	Intermediate Similarity	NPC60772
0.7458	Intermediate Similarity	NPC236623
0.7458	Intermediate Similarity	NPC64866
0.7429	Intermediate Similarity	NPC223187
0.7424	Intermediate Similarity	NPC469662
0.7419	Intermediate Similarity	NPC473733
0.7397	Intermediate Similarity	NPC276769
0.7391	Intermediate Similarity	NPC477857
0.7377	Intermediate Similarity	NPC95581
0.7368	Intermediate Similarity	NPC142253
0.7368	Intermediate Similarity	NPC3511
0.7368	Intermediate Similarity	NPC8610
0.7368	Intermediate Similarity	NPC262558
0.7368	Intermediate Similarity	NPC472239
0.7361	Intermediate Similarity	NPC473171
0.7333	Intermediate Similarity	NPC164218
0.7324	Intermediate Similarity	NPC300940
0.7297	Intermediate Similarity	NPC474056
0.7297	Intermediate Similarity	NPC469996
0.7288	Intermediate Similarity	NPC228776
0.7288	Intermediate Similarity	NPC163984
0.7288	Intermediate Similarity	NPC58970
0.7288	Intermediate Similarity	NPC116906
0.7288	Intermediate Similarity	NPC176819
0.726	Intermediate Similarity	NPC226242
0.7258	Intermediate Similarity	NPC188789
0.7258	Intermediate Similarity	NPC200258
0.7246	Intermediate Similarity	NPC476614
0.7237	Intermediate Similarity	NPC477372
0.7222	Intermediate Similarity	NPC20025
0.7213	Intermediate Similarity	NPC14002
0.7213	Intermediate Similarity	NPC37644
0.7206	Intermediate Similarity	NPC43300
0.7206	Intermediate Similarity	NPC96812
0.7206	Intermediate Similarity	NPC168824
0.7206	Intermediate Similarity	NPC107704
0.7206	Intermediate Similarity	NPC189917
0.7206	Intermediate Similarity	NPC39462
0.72	Intermediate Similarity	NPC469690
0.72	Intermediate Similarity	NPC261125
0.72	Intermediate Similarity	NPC181195
0.7193	Intermediate Similarity	NPC49088
0.7183	Intermediate Similarity	NPC190035
0.7183	Intermediate Similarity	NPC225467
0.7183	Intermediate Similarity	NPC21944
0.7183	Intermediate Similarity	NPC133253
0.7183	Intermediate Similarity	NPC474562
0.7183	Intermediate Similarity	NPC469737
0.7179	Intermediate Similarity	NPC181743
0.7179	Intermediate Similarity	NPC238197
0.7179	Intermediate Similarity	NPC87552
0.7179	Intermediate Similarity	NPC178025
0.7179	Intermediate Similarity	NPC16287
0.7164	Intermediate Similarity	NPC4638
0.7164	Intermediate Similarity	NPC150162
0.7162	Intermediate Similarity	NPC91665
0.7143	Intermediate Similarity	NPC320514
0.7143	Intermediate Similarity	NPC469805
0.7143	Intermediate Similarity	NPC472867
0.7143	Intermediate Similarity	NPC469799
0.7143	Intermediate Similarity	NPC256750
0.7143	Intermediate Similarity	NPC193347
0.7143	Intermediate Similarity	NPC20262
0.7143	Intermediate Similarity	NPC469804
0.7143	Intermediate Similarity	NPC469806
0.7123	Intermediate Similarity	NPC476346
0.7123	Intermediate Similarity	NPC474011
0.7123	Intermediate Similarity	NPC216791
0.7121	Intermediate Similarity	NPC260573
0.7105	Intermediate Similarity	NPC469797
0.7105	Intermediate Similarity	NPC472478
0.7105	Intermediate Similarity	NPC45495
0.7105	Intermediate Similarity	NPC469798
0.7101	Intermediate Similarity	NPC290350
0.7101	Intermediate Similarity	NPC4370

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 NPC25853 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	3187
0.2-0.3	4199
0.3-0.4	1027
0.4-0.5	262
0.5-0.6	186
0.6-0.7	69
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
0.8333	Intermediate Similarity	NPD4747	Approved
0.8333	Intermediate Similarity	NPD4691	Approved
0.8209	Intermediate Similarity	NPD5276	Approved
0.8182	Intermediate Similarity	NPD4137	Phase 3
0.7971	Intermediate Similarity	NPD4058	Approved
0.7971	Intermediate Similarity	NPD4687	Approved
0.7971	Intermediate Similarity	NPD5733	Approved
0.7761	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD287	Approved
0.7143	Intermediate Similarity	NPD4223	Phase 3
0.7143	Intermediate Similarity	NPD4221	Approved
0.7051	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5690	Phase 2
0.6962	Remote Similarity	NPD4197	Approved
0.6875	Remote Similarity	NPD5329	Approved
0.6842	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4690	Approved
0.679	Remote Similarity	NPD4693	Phase 3
0.679	Remote Similarity	NPD5205	Approved
0.679	Remote Similarity	NPD4694	Approved
0.679	Remote Similarity	NPD4688	Approved
0.679	Remote Similarity	NPD5280	Approved
0.679	Remote Similarity	NPD4138	Approved
0.679	Remote Similarity	NPD5279	Phase 3
0.679	Remote Similarity	NPD4689	Approved
0.678	Remote Similarity	NPD344	Approved
0.678	Remote Similarity	NPD343	Approved
0.678	Remote Similarity	NPD345	Approved
0.675	Remote Similarity	NPD3133	Approved
0.675	Remote Similarity	NPD3666	Approved
0.675	Remote Similarity	NPD3665	Phase 1
0.6714	Remote Similarity	NPD7331	Phase 2
0.6667	Remote Similarity	NPD4695	Discontinued
0.6627	Remote Similarity	NPD6672	Approved
0.6627	Remote Similarity	NPD5208	Approved
0.6627	Remote Similarity	NPD5737	Approved
0.6627	Remote Similarity	NPD4518	Approved
0.6623	Remote Similarity	NPD3617	Approved
0.6588	Remote Similarity	NPD6079	Approved
0.6585	Remote Similarity	NPD3618	Phase 1
0.6585	Remote Similarity	NPD7521	Approved
0.6585	Remote Similarity	NPD7334	Approved
0.6585	Remote Similarity	NPD7146	Approved
0.6585	Remote Similarity	NPD6409	Approved
0.6585	Remote Similarity	NPD6684	Approved
0.6585	Remote Similarity	NPD5330	Approved
0.6585	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4753	Phase 2
0.6548	Remote Similarity	NPD6904	Approved
0.6548	Remote Similarity	NPD5328	Approved
0.6548	Remote Similarity	NPD6673	Approved
0.6548	Remote Similarity	NPD6080	Approved
0.6543	Remote Similarity	NPD4786	Approved
0.6538	Remote Similarity	NPD4195	Approved
0.65	Remote Similarity	NPD3667	Approved
0.6471	Remote Similarity	NPD4096	Approved
0.6471	Remote Similarity	NPD5692	Phase 3
0.6471	Remote Similarity	NPD5207	Approved
0.6429	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6903	Approved
0.6395	Remote Similarity	NPD5284	Approved
0.6395	Remote Similarity	NPD5694	Approved
0.6395	Remote Similarity	NPD6050	Approved
0.6395	Remote Similarity	NPD5281	Approved
0.6395	Remote Similarity	NPD5693	Phase 1
0.6386	Remote Similarity	NPD6098	Approved
0.6375	Remote Similarity	NPD8028	Phase 2
0.6364	Remote Similarity	NPD5210	Approved
0.6364	Remote Similarity	NPD4629	Approved
0.6341	Remote Similarity	NPD3668	Phase 3
0.6338	Remote Similarity	NPD7341	Phase 2
0.6322	Remote Similarity	NPD4202	Approved
0.6296	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD5222	Approved
0.6292	Remote Similarity	NPD5221	Approved
0.6279	Remote Similarity	NPD5785	Approved
0.6265	Remote Similarity	NPD5363	Approved
0.625	Remote Similarity	NPD6001	Approved
0.6222	Remote Similarity	NPD5173	Approved
0.622	Remote Similarity	NPD4788	Approved
0.619	Remote Similarity	NPD4519	Discontinued
0.619	Remote Similarity	NPD4623	Approved
0.618	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.618	Remote Similarity	NPD5695	Phase 3
0.6173	Remote Similarity	NPD4139	Approved
0.6173	Remote Similarity	NPD4692	Approved
0.614	Remote Similarity	NPD5783	Phase 3
0.6136	Remote Similarity	NPD5133	Approved
0.6118	Remote Similarity	NPD3573	Approved
0.6111	Remote Similarity	NPD4697	Phase 3
0.6098	Remote Similarity	NPD5209	Approved
0.6087	Remote Similarity	NPD4696	Approved
0.6087	Remote Similarity	NPD5285	Approved
0.6087	Remote Similarity	NPD5286	Approved
0.6071	Remote Similarity	NPD1694	Approved
0.6056	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD5368	Approved
0.6044	Remote Similarity	NPD6083	Phase 2
0.6044	Remote Similarity	NPD6084	Phase 2
0.6044	Remote Similarity	NPD4755	Approved
0.6027	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD5362	Discontinued
0.6022	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD5654	Approved
0.6	Remote Similarity	NPD6923	Approved
0.6	Remote Similarity	NPD6922	Approved
0.5978	Remote Similarity	NPD5696	Approved
0.5976	Remote Similarity	NPD5369	Approved
0.597	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5091	Approved
0.5957	Remote Similarity	NPD5211	Phase 2
0.5957	Remote Similarity	NPD5225	Approved
0.5957	Remote Similarity	NPD5224	Approved
0.5957	Remote Similarity	NPD5226	Approved
0.5957	Remote Similarity	NPD4633	Approved
0.5955	Remote Similarity	NPD6399	Phase 3
0.5921	Remote Similarity	NPD7144	Approved
0.5921	Remote Similarity	NPD7143	Approved
0.5915	Remote Similarity	NPD4192	Approved
0.5915	Remote Similarity	NPD4194	Approved
0.5915	Remote Similarity	NPD4193	Approved
0.5915	Remote Similarity	NPD4191	Approved
0.5914	Remote Similarity	NPD4700	Approved
0.5904	Remote Similarity	NPD4270	Approved
0.5904	Remote Similarity	NPD4269	Approved
0.5904	Remote Similarity	NPD6435	Approved
0.5895	Remote Similarity	NPD5174	Approved
0.5895	Remote Similarity	NPD5175	Approved
0.587	Remote Similarity	NPD5959	Approved
0.5854	Remote Similarity	NPD4252	Approved
0.5854	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD7152	Approved
0.5844	Remote Similarity	NPD7151	Approved
0.5844	Remote Similarity	NPD7150	Approved
0.5844	Remote Similarity	NPD4243	Approved
0.5833	Remote Similarity	NPD5141	Approved
0.5783	Remote Similarity	NPD857	Phase 3
0.5745	Remote Similarity	NPD6404	Discontinued
0.5729	Remote Similarity	NPD4754	Approved
0.5729	Remote Similarity	NPD6052	Approved
0.5714	Remote Similarity	NPD5282	Discontinued
0.5714	Remote Similarity	NPD5697	Approved
0.5714	Remote Similarity	NPD6614	Approved
0.5714	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD4785	Approved
0.5696	Remote Similarity	NPD4784	Approved
0.5696	Remote Similarity	NPD6924	Approved
0.5696	Remote Similarity	NPD6926	Approved
0.5667	Remote Similarity	NPD7515	Phase 2
0.5657	Remote Similarity	NPD5168	Approved
0.5657	Remote Similarity	NPD4730	Approved
0.5657	Remote Similarity	NPD6899	Approved
0.5657	Remote Similarity	NPD6011	Approved
0.5657	Remote Similarity	NPD6881	Approved
0.5657	Remote Similarity	NPD5128	Approved
0.5657	Remote Similarity	NPD4729	Approved
0.5652	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD5332	Approved
0.5647	Remote Similarity	NPD5331	Approved
0.5632	Remote Similarity	NPD5786	Approved
0.5625	Remote Similarity	NPD4190	Phase 3
0.5625	Remote Similarity	NPD7339	Approved
0.5625	Remote Similarity	NPD6942	Approved
0.5625	Remote Similarity	NPD5275	Approved
0.5625	Remote Similarity	NPD8039	Approved
0.5618	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD1695	Approved
0.5612	Remote Similarity	NPD4768	Approved
0.5612	Remote Similarity	NPD5739	Approved
0.5612	Remote Similarity	NPD6402	Approved
0.5612	Remote Similarity	NPD6008	Approved
0.5612	Remote Similarity	NPD7128	Approved
0.5612	Remote Similarity	NPD4767	Approved
0.5612	Remote Similarity	NPD6675	Approved
0.5606	Remote Similarity	NPD28	Approved
0.5606	Remote Similarity	NPD29	Approved
0.5604	Remote Similarity	NPD1508	Approved
0.56	Remote Similarity	NPD6012	Approved
0.56	Remote Similarity	NPD6013	Approved
0.56	Remote Similarity	NPD6014	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