NPASS Compound

Structure

NPC250315 OpenBabel07101718222D 23 24 0 0 1 0 0 0 0 0999 V2000 -6.2497 -0.8545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3981 -2.3510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0773 2.5865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1856 3.3354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8895 -1.8154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1731 1.4552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7555 -1.3154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8923 -1.8901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4679 0.4997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6989 1.9789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4930 2.1883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5649 2.4789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2812 -0.7918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3188 -0.4892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9614 -1.5248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2412 1.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1355 1.1526 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9865 0.1638 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4606 0.8876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5621 2.5536 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4495 1.0366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1967 3.4845 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 2 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 11 2 0 0 0 0 7 14 2 0 0 0 0 8 15 1 0 0 0 0 9 14 1 0 0 0 0 10 12 1 0 0 0 0 11 20 1 0 0 0 0 12 20 1 0 0 0 0 13 15 2 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 10 1 1 0 0 0 17 18 1 0 0 0 0 18 13 1 1 0 0 0 18 23 1 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 20 4 1 1 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	350.552
LogP:	3.431
LogD:	3.436
LogS:	-4.616
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.413
Synthetic Accessibility Score:	4.775
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.687
MDCK Permeability:	1.8344180716667324e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.954
20% Bioavailability (F20%):	0.705
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	90.10294342041016%
Volume Distribution (VD):	0.417
Pgp-substrate:	1.8305469751358032%

ADMET: Metabolism

CYP1A2-inhibitor:	0.319
CYP1A2-substrate:	0.279
CYP2C19-inhibitor:	0.854
CYP2C19-substrate:	0.324
CYP2C9-inhibitor:	0.701
CYP2C9-substrate:	0.705
CYP2D6-inhibitor:	0.653
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.861
CYP3A4-substrate:	0.178

ADMET: Excretion

Clearance (CL):	3.973
Half-life (T1/2):	0.431

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.323
Drug-inuced Liver Injury (DILI):	0.339
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.292
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.917
Carcinogencity:	0.068
Eye Corrosion:	0.059
Eye Irritation:	0.13
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC250315

Natural Product ID:	NPC250315
*Common Name:**	Crassumolide D
IUPAC Name:	(3aS,6R,7E,10E,14E,15aS)-6-hydroxy-6,10,14-trimethyl-3-methylidene-4,5,9,12,13,15a-hexahydro-3aH-cyclotetradeca[b]furan-2-one
Synonyms:	Crassumolide D
Standard InCHIKey:	KJXGGBUBHZLVAV-FTHBWNQNSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-14-7-5-8-15(2)13-18-17(16(3)19(21)23-18)10-12-20(4,22)11-6-9-14/h6-7,11,13,17-18,22H,3,5,8-10,12H2,1-2,4H3/b11-6+,14-7+,15-13+/t17-,18-,20-/m0/s1
SMILES:	C/C/1=C[C@@H]2OC(=O)C(=C)[C@@H]2CC[C@@](/C=C/C/C(=C/CC1)/C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL572861
PubChem CID:	25156699
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones [CHEMONTID:0002502] Cembranolides

*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
NPO27251	Lobophytum crassum	Species	Alcyoniidae	Eukaryota	n.a.	south china sea	n.a.	PMID[18512986]
NPO27251	Lobophytum crassum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18973388]
NPO27251	Lobophytum crassum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548852]
NPO27251	Lobophytum crassum	Species	Alcyoniidae	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	6

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[518264]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[518264]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[518264]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[518264]
NPT1031	Cell Line	Ca9-22	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[518264]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	5.0	ug.mL-1	PMID[518264]

☑ 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 NPC250315 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	171
0.1-0.2	1080
0.2-0.3	4634
0.3-0.4	10751
0.4-0.5	13395
0.5-0.6	7184
0.6-0.7	4136
0.7-0.8	1133
0.8-0.85	163
0.85-0.9	43
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9506	High Similarity	NPC160138
0.9351	High Similarity	NPC267231
0.9167	High Similarity	NPC179394
0.9167	High Similarity	NPC475855
0.9167	High Similarity	NPC144133
0.9024	High Similarity	NPC215364
0.9	High Similarity	NPC325031
0.8974	High Similarity	NPC7563
0.8974	High Similarity	NPC116177
0.8974	High Similarity	NPC320630
0.8861	High Similarity	NPC108816
0.8861	High Similarity	NPC93763
0.8824	High Similarity	NPC295312
0.875	High Similarity	NPC304886
0.8736	High Similarity	NPC228451
0.8736	High Similarity	NPC125674
0.8736	High Similarity	NPC475912
0.8736	High Similarity	NPC475838
0.8721	High Similarity	NPC476004
0.8721	High Similarity	NPC474761
0.8721	High Similarity	NPC51004
0.8706	High Similarity	NPC202672
0.8636	High Similarity	NPC81386
0.8636	High Similarity	NPC474035
0.8636	High Similarity	NPC474338
0.8636	High Similarity	NPC474247
0.8625	High Similarity	NPC471465
0.8625	High Similarity	NPC196653
0.8621	High Similarity	NPC30515
0.8605	High Similarity	NPC474032
0.8605	High Similarity	NPC307411
0.8571	High Similarity	NPC21469
0.8571	High Similarity	NPC163003
0.8571	High Similarity	NPC255307
0.8556	High Similarity	NPC471462
0.8554	High Similarity	NPC272814
0.8554	High Similarity	NPC473390
0.8554	High Similarity	NPC131669
0.8539	High Similarity	NPC270013
0.8539	High Similarity	NPC36954
0.8539	High Similarity	NPC14961
0.8523	High Similarity	NPC179746
0.8523	High Similarity	NPC476300
0.8523	High Similarity	NPC81419
0.8519	High Similarity	NPC470239
0.8519	High Similarity	NPC470244
0.8506	High Similarity	NPC37607
0.8506	High Similarity	NPC301969
0.8488	Intermediate Similarity	NPC91248
0.8471	Intermediate Similarity	NPC67493
0.8471	Intermediate Similarity	NPC305475
0.8471	Intermediate Similarity	NPC475461
0.8471	Intermediate Similarity	NPC284902
0.8471	Intermediate Similarity	NPC50637
0.8452	Intermediate Similarity	NPC476804
0.8452	Intermediate Similarity	NPC114979
0.8452	Intermediate Similarity	NPC191476
0.8444	Intermediate Similarity	NPC476315
0.8444	Intermediate Similarity	NPC279621
0.8444	Intermediate Similarity	NPC230800
0.8434	Intermediate Similarity	NPC229825
0.8427	Intermediate Similarity	NPC323008
0.8427	Intermediate Similarity	NPC198853
0.8427	Intermediate Similarity	NPC470013
0.8427	Intermediate Similarity	NPC470010
0.8427	Intermediate Similarity	NPC262133
0.8427	Intermediate Similarity	NPC477131
0.8409	Intermediate Similarity	NPC133698
0.8409	Intermediate Similarity	NPC184463
0.8409	Intermediate Similarity	NPC208886
0.8409	Intermediate Similarity	NPC12172
0.8375	Intermediate Similarity	NPC235906
0.8372	Intermediate Similarity	NPC231889
0.8372	Intermediate Similarity	NPC475703
0.8354	Intermediate Similarity	NPC476355
0.8354	Intermediate Similarity	NPC140287
0.8353	Intermediate Similarity	NPC137033
0.8353	Intermediate Similarity	NPC165162
0.8333	Intermediate Similarity	NPC169575
0.8333	Intermediate Similarity	NPC40746
0.8333	Intermediate Similarity	NPC67584
0.8333	Intermediate Similarity	NPC318468
0.8315	Intermediate Similarity	NPC212486
0.8315	Intermediate Similarity	NPC476049
0.8313	Intermediate Similarity	NPC141810
0.8313	Intermediate Similarity	NPC24417
0.8295	Intermediate Similarity	NPC473448
0.8293	Intermediate Similarity	NPC89128
0.8293	Intermediate Similarity	NPC167881
0.8293	Intermediate Similarity	NPC98557
0.8293	Intermediate Similarity	NPC617
0.8276	Intermediate Similarity	NPC153805
0.8276	Intermediate Similarity	NPC473715
0.8276	Intermediate Similarity	NPC227379
0.8276	Intermediate Similarity	NPC474471
0.8272	Intermediate Similarity	NPC65603
0.8272	Intermediate Similarity	NPC476794
0.8272	Intermediate Similarity	NPC470240
0.8261	Intermediate Similarity	NPC187268
0.8256	Intermediate Similarity	NPC122502
0.8242	Intermediate Similarity	NPC213078
0.8235	Intermediate Similarity	NPC96259
0.8235	Intermediate Similarity	NPC141193
0.8235	Intermediate Similarity	NPC472957
0.8235	Intermediate Similarity	NPC158756
0.8235	Intermediate Similarity	NPC472958
0.8228	Intermediate Similarity	NPC295633
0.8228	Intermediate Similarity	NPC269206
0.8228	Intermediate Similarity	NPC58956
0.8222	Intermediate Similarity	NPC127019
0.8222	Intermediate Similarity	NPC303942
0.8222	Intermediate Similarity	NPC57405
0.8202	Intermediate Similarity	NPC131209
0.8202	Intermediate Similarity	NPC300312
0.8202	Intermediate Similarity	NPC111114
0.8202	Intermediate Similarity	NPC473321
0.8202	Intermediate Similarity	NPC261607
0.8182	Intermediate Similarity	NPC166919
0.8172	Intermediate Similarity	NPC288876
0.8161	Intermediate Similarity	NPC72513
0.8152	Intermediate Similarity	NPC161493
0.8148	Intermediate Similarity	NPC123360
0.814	Intermediate Similarity	NPC470755
0.814	Intermediate Similarity	NPC261380
0.814	Intermediate Similarity	NPC235792
0.8132	Intermediate Similarity	NPC474947
0.8132	Intermediate Similarity	NPC52044
0.8132	Intermediate Similarity	NPC272050
0.8132	Intermediate Similarity	NPC213698
0.8132	Intermediate Similarity	NPC107476
0.8132	Intermediate Similarity	NPC471142
0.8132	Intermediate Similarity	NPC170120
0.8132	Intermediate Similarity	NPC471141
0.8132	Intermediate Similarity	NPC475659
0.8118	Intermediate Similarity	NPC116543
0.8118	Intermediate Similarity	NPC11620
0.8118	Intermediate Similarity	NPC170286
0.8111	Intermediate Similarity	NPC135776
0.8095	Intermediate Similarity	NPC25684
0.8095	Intermediate Similarity	NPC281949
0.8095	Intermediate Similarity	NPC52861
0.8095	Intermediate Similarity	NPC301477
0.809	Intermediate Similarity	NPC473619
0.809	Intermediate Similarity	NPC106510
0.809	Intermediate Similarity	NPC62815
0.809	Intermediate Similarity	NPC71533
0.809	Intermediate Similarity	NPC469368
0.809	Intermediate Similarity	NPC158488
0.809	Intermediate Similarity	NPC475748
0.8085	Intermediate Similarity	NPC474742
0.8085	Intermediate Similarity	NPC150923
0.8072	Intermediate Similarity	NPC469617
0.8068	Intermediate Similarity	NPC476803
0.8068	Intermediate Similarity	NPC475819
0.8068	Intermediate Similarity	NPC476805
0.8065	Intermediate Similarity	NPC221615
0.8049	Intermediate Similarity	NPC141789
0.8049	Intermediate Similarity	NPC41780
0.8049	Intermediate Similarity	NPC187568
0.8049	Intermediate Similarity	NPC476028
0.8049	Intermediate Similarity	NPC171204
0.8049	Intermediate Similarity	NPC97516
0.8046	Intermediate Similarity	NPC162071
0.8046	Intermediate Similarity	NPC469910
0.8046	Intermediate Similarity	NPC150755
0.8043	Intermediate Similarity	NPC473859
0.8025	Intermediate Similarity	NPC193351
0.8025	Intermediate Similarity	NPC226669
0.8025	Intermediate Similarity	NPC138408
0.8025	Intermediate Similarity	NPC155587
0.8025	Intermediate Similarity	NPC329852
0.8023	Intermediate Similarity	NPC156485
0.8023	Intermediate Similarity	NPC474780
0.8023	Intermediate Similarity	NPC295799
0.8022	Intermediate Similarity	NPC167219
0.8	Intermediate Similarity	NPC85772
0.8	Intermediate Similarity	NPC189609
0.8	Intermediate Similarity	NPC474291
0.8	Intermediate Similarity	NPC197835
0.8	Intermediate Similarity	NPC291500
0.8	Intermediate Similarity	NPC20713
0.8	Intermediate Similarity	NPC303653
0.8	Intermediate Similarity	NPC475925
0.8	Intermediate Similarity	NPC86077
0.8	Intermediate Similarity	NPC140591
0.8	Intermediate Similarity	NPC149371
0.8	Intermediate Similarity	NPC89555
0.7978	Intermediate Similarity	NPC218927
0.7978	Intermediate Similarity	NPC206001
0.7978	Intermediate Similarity	NPC151770
0.7978	Intermediate Similarity	NPC473564
0.7978	Intermediate Similarity	NPC212598
0.7978	Intermediate Similarity	NPC268298
0.7955	Intermediate Similarity	NPC248602
0.7955	Intermediate Similarity	NPC186148
0.7935	Intermediate Similarity	NPC477922
0.7931	Intermediate Similarity	NPC284534
0.7931	Intermediate Similarity	NPC38468
0.7931	Intermediate Similarity	NPC474547
0.7931	Intermediate Similarity	NPC204105

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 NPC250315 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1580
0.2-0.3	3729
0.3-0.4	2446
0.4-0.5	798
0.5-0.6	361
0.6-0.7	57
0.7-0.8	25
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
0.7931	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1695	Approved
0.75	Intermediate Similarity	NPD46	Approved
0.75	Intermediate Similarity	NPD7154	Phase 3
0.75	Intermediate Similarity	NPD5785	Approved
0.75	Intermediate Similarity	NPD6698	Approved
0.75	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5363	Approved
0.7333	Intermediate Similarity	NPD1694	Approved
0.732	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7838	Discovery
0.7303	Intermediate Similarity	NPD5362	Discontinued
0.7282	Intermediate Similarity	NPD6371	Approved
0.7253	Intermediate Similarity	NPD4249	Approved
0.7234	Intermediate Similarity	NPD7983	Approved
0.7212	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4270	Approved
0.7191	Intermediate Similarity	NPD4269	Approved
0.7174	Intermediate Similarity	NPD4251	Approved
0.7174	Intermediate Similarity	NPD4250	Approved
0.7158	Intermediate Similarity	NPD5779	Approved
0.7158	Intermediate Similarity	NPD5778	Approved
0.7083	Intermediate Similarity	NPD5282	Discontinued
0.7079	Intermediate Similarity	NPD5369	Approved
0.7065	Intermediate Similarity	NPD5786	Approved
0.7	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4225	Approved
0.6966	Remote Similarity	NPD4819	Approved
0.6966	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4822	Approved
0.6966	Remote Similarity	NPD4821	Approved
0.6966	Remote Similarity	NPD4820	Approved
0.6966	Remote Similarity	NPD4252	Approved
0.6932	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7640	Approved
0.69	Remote Similarity	NPD7639	Approved
0.6832	Remote Similarity	NPD5344	Discontinued
0.68	Remote Similarity	NPD7638	Approved
0.6782	Remote Similarity	NPD8039	Approved
0.6774	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7839	Suspended
0.6762	Remote Similarity	NPD6686	Approved
0.6742	Remote Similarity	NPD4268	Approved
0.6742	Remote Similarity	NPD4271	Approved
0.6739	Remote Similarity	NPD5332	Approved
0.6739	Remote Similarity	NPD5331	Approved
0.6733	Remote Similarity	NPD6648	Approved
0.6703	Remote Similarity	NPD4790	Discontinued
0.6667	Remote Similarity	NPD6053	Discontinued
0.663	Remote Similarity	NPD5209	Approved
0.663	Remote Similarity	NPD6435	Approved
0.6577	Remote Similarity	NPD7115	Discovery
0.6548	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7637	Suspended
0.6495	Remote Similarity	NPD5370	Suspended
0.6495	Remote Similarity	NPD6101	Approved
0.6495	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD8517	Approved
0.6491	Remote Similarity	NPD8513	Phase 3
0.6491	Remote Similarity	NPD8515	Approved
0.6491	Remote Similarity	NPD8516	Approved
0.6465	Remote Similarity	NPD6399	Phase 3
0.6444	Remote Similarity	NPD4756	Discovery
0.642	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD5368	Approved
0.6364	Remote Similarity	NPD6411	Approved
0.6364	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7632	Discontinued
0.6262	Remote Similarity	NPD6008	Approved
0.6239	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD7331	Phase 2
0.6218	Remote Similarity	NPD8074	Phase 3
0.6211	Remote Similarity	NPD6110	Phase 1
0.619	Remote Similarity	NPD3197	Phase 1
0.6186	Remote Similarity	NPD4519	Discontinued
0.6186	Remote Similarity	NPD7334	Approved
0.6186	Remote Similarity	NPD4623	Approved
0.6186	Remote Similarity	NPD7146	Approved
0.6186	Remote Similarity	NPD6684	Approved
0.6186	Remote Similarity	NPD7521	Approved
0.6186	Remote Similarity	NPD5330	Approved
0.6186	Remote Similarity	NPD6409	Approved
0.6176	Remote Similarity	NPD5695	Phase 3
0.6154	Remote Similarity	NPD3172	Approved
0.6154	Remote Similarity	NPD5696	Approved
0.6118	Remote Similarity	NPD7341	Phase 2
0.6105	Remote Similarity	NPD3667	Approved
0.61	Remote Similarity	NPD5207	Approved
0.6078	Remote Similarity	NPD7748	Approved
0.6076	Remote Similarity	NPD3195	Phase 2
0.6076	Remote Similarity	NPD3196	Approved
0.6076	Remote Similarity	NPD4266	Approved
0.6076	Remote Similarity	NPD3194	Approved
0.6061	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6903	Approved
0.6058	Remote Similarity	NPD6083	Phase 2
0.6058	Remote Similarity	NPD6084	Phase 2
0.6058	Remote Similarity	NPD7902	Approved
0.6055	Remote Similarity	NPD5697	Approved
0.6055	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD6695	Phase 3
0.604	Remote Similarity	NPD5281	Approved
0.604	Remote Similarity	NPD5284	Approved
0.604	Remote Similarity	NPD5693	Phase 1
0.602	Remote Similarity	NPD6422	Discontinued
0.602	Remote Similarity	NPD3618	Phase 1
0.6018	Remote Similarity	NPD4632	Approved
0.6016	Remote Similarity	NPD7260	Phase 2
0.6	Remote Similarity	NPD6899	Approved
0.6	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD7500	Approved
0.6	Remote Similarity	NPD8273	Phase 1
0.6	Remote Similarity	NPD6881	Approved
0.5982	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6650	Approved
0.5982	Remote Similarity	NPD6649	Approved
0.5979	Remote Similarity	NPD4786	Approved
0.5979	Remote Similarity	NPD3133	Approved
0.5979	Remote Similarity	NPD3666	Approved
0.5979	Remote Similarity	NPD3665	Phase 1
0.5979	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD7642	Approved
0.596	Remote Similarity	NPD3573	Approved
0.5952	Remote Similarity	NPD368	Approved
0.5946	Remote Similarity	NPD6012	Approved
0.5946	Remote Similarity	NPD6013	Approved
0.5946	Remote Similarity	NPD6014	Approved
0.5926	Remote Similarity	NPD6647	Phase 2
0.5906	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.59	Remote Similarity	NPD5737	Approved
0.59	Remote Similarity	NPD6672	Approved
0.5897	Remote Similarity	NPD6927	Phase 3
0.5895	Remote Similarity	NPD6931	Approved
0.5895	Remote Similarity	NPD7514	Phase 3
0.5895	Remote Similarity	NPD4695	Discontinued
0.5895	Remote Similarity	NPD6930	Phase 2
0.5895	Remote Similarity	NPD7332	Phase 2
0.5893	Remote Similarity	NPD7102	Approved
0.5893	Remote Similarity	NPD6421	Discontinued
0.5893	Remote Similarity	NPD7290	Approved
0.5893	Remote Similarity	NPD6883	Approved
0.5882	Remote Similarity	NPD6079	Approved
0.5882	Remote Similarity	NPD7515	Phase 2
0.5868	Remote Similarity	NPD7507	Approved
0.5868	Remote Similarity	NPD8451	Approved
0.5865	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD4629	Approved
0.5865	Remote Similarity	NPD5210	Approved
0.5862	Remote Similarity	NPD6009	Approved
0.5859	Remote Similarity	NPD5279	Phase 3
0.5859	Remote Similarity	NPD5690	Phase 2
0.5856	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD6319	Approved
0.5844	Remote Similarity	NPD3173	Approved
0.5842	Remote Similarity	NPD6051	Approved
0.5841	Remote Similarity	NPD6847	Approved
0.5841	Remote Similarity	NPD6869	Approved
0.5841	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD8130	Phase 1
0.5841	Remote Similarity	NPD6617	Approved
0.5841	Remote Similarity	NPD2204	Approved
0.5833	Remote Similarity	NPD7830	Approved
0.5833	Remote Similarity	NPD5211	Phase 2
0.5833	Remote Similarity	NPD7829	Approved
0.5825	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD4732	Discontinued
0.582	Remote Similarity	NPD8448	Approved
0.5818	Remote Similarity	NPD6675	Approved
0.5818	Remote Similarity	NPD7128	Approved
0.5818	Remote Similarity	NPD5739	Approved
0.5818	Remote Similarity	NPD6402	Approved
0.5814	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD7641	Discontinued
0.581	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD6373	Approved
0.5804	Remote Similarity	NPD6372	Approved
0.5804	Remote Similarity	NPD6413	Approved
0.5802	Remote Similarity	NPD342	Phase 1
0.58	Remote Similarity	NPD7524	Approved
0.58	Remote Similarity	NPD7750	Discontinued
0.5798	Remote Similarity	NPD5983	Phase 2
0.5789	Remote Similarity	NPD6929	Approved
0.5789	Remote Similarity	NPD6882	Approved
0.5789	Remote Similarity	NPD8297	Approved
0.5785	Remote Similarity	NPD8341	Approved
0.5785	Remote Similarity	NPD7492	Approved
0.5785	Remote Similarity	NPD8340	Approved
0.5785	Remote Similarity	NPD8299	Approved
0.5785	Remote Similarity	NPD8342	Approved
0.5773	Remote Similarity	NPD4221	Approved
0.5773	Remote Similarity	NPD4223	Phase 3
0.5773	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6001	Approved
0.5769	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7900	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