NPASS Compound

Structure

CID320630 OpenBabel06191716152D 23 24 0 0 1 0 0 0 0 0999 V2000 -2.6836 4.3088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1478 1.3084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6830 1.3080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3084 2.5688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4156 3.3086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5498 2.8088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2815 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8170 2.8085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8169 1.8083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4160 1.3085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8173 -0.1918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6836 3.3088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2817 1.8083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0004 1.6176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4157 0.3087 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9512 1.3084 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9509 0.3087 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5874 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2817 -0.1914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5875 0.8092 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 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 2 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 1 0 0 0 0 7 14 2 0 0 0 0 8 9 1 0 0 0 0 8 13 2 0 0 0 0 10 14 1 0 0 0 0 10 17 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 1 0 0 0 18 9 1 6 0 0 0 18 19 1 0 0 0 0 19 12 1 1 0 0 0 19 23 1 0 0 0 0 20 22 2 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	350.552
LogP:	4.042
LogD:	3.859
LogS:	-4.685
# 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:	4.645
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.709
MDCK Permeability:	3.997118619736284e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.984
20% Bioavailability (F20%):	0.781
30% Bioavailability (F30%):	0.746

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.084
Plasma Protein Binding (PPB):	92.38807678222656%
Volume Distribution (VD):	0.261
Pgp-substrate:	2.4150002002716064%

ADMET: Metabolism

CYP1A2-inhibitor:	0.078
CYP1A2-substrate:	0.085
CYP2C19-inhibitor:	0.284
CYP2C19-substrate:	0.084
CYP2C9-inhibitor:	0.399
CYP2C9-substrate:	0.13
CYP2D6-inhibitor:	0.419
CYP2D6-substrate:	0.304
CYP3A4-inhibitor:	0.409
CYP3A4-substrate:	0.244

ADMET: Excretion

Clearance (CL):	8.041
Half-life (T1/2):	0.577

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.231
Drug-inuced Liver Injury (DILI):	0.307
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.959
Carcinogencity:	0.072
Eye Corrosion:	0.027
Eye Irritation:	0.569
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC320630

Natural Product ID:	NPC320630
*Common Name:**	Crassumolide A
IUPAC Name:	(3aR,5E,9E,12S,13E,15aS)-12-hydroxy-6,10,14-trimethyl-3-methylidene-3a,4,7,8,11,12,15,15a-octahydrocyclotetradeca[b]furan-2-one
Synonyms:
Standard InCHIKey:	BIDNFRVXQJTBCI-XXYAPWOQSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-13-6-5-7-14(2)10-17(21)11-15(3)12-19-18(9-8-13)16(4)20(22)23-19/h7-8,11,17-19,21H,4-6,9-10,12H2,1-3H3/b13-8+,14-7+,15-11+/t17-,18+,19-/m0/s1
SMILES:	C/C/1=CC[C@H]2[C@H](C/C(=C/[C@H](C/C(=C/CC1)/C)O)/C)OC(=O)C2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL577584
PubChem CID:	25156430
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
Others	2

Activity Type	# Activity
Cell Line	7
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[483242]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[483242]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[483242]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[483242]
NPT1031	Cell Line	Ca9-22	Homo sapiens	IC50	=	3.2	ug.mL-1	PMID[483242]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	26.8	%	PMID[483242]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	50.2	%	PMID[483242]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	5.0	ug.mL-1	PMID[483242]

☑ 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 NPC320630 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	153
0.1-0.2	1085
0.2-0.3	5156
0.3-0.4	14335
0.4-0.5	10949
0.5-0.6	6350
0.6-0.7	3498
0.7-0.8	978
0.8-0.85	97
0.85-0.9	69
0.9-0.95	19
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC7563
1.0	High Similarity	NPC116177
0.9589	High Similarity	NPC108816
0.9589	High Similarity	NPC93763
0.9589	High Similarity	NPC267231
0.9589	High Similarity	NPC471465
0.9589	High Similarity	NPC196653
0.9296	High Similarity	NPC163003
0.9221	High Similarity	NPC40746
0.9221	High Similarity	NPC169575
0.9221	High Similarity	NPC131669
0.9221	High Similarity	NPC473390
0.9211	High Similarity	NPC24417
0.92	High Similarity	NPC98557
0.92	High Similarity	NPC167881
0.9103	High Similarity	NPC476804
0.9103	High Similarity	NPC158756
0.9091	High Similarity	NPC229825
0.9041	High Similarity	NPC476355
0.9041	High Similarity	NPC140287
0.8987	High Similarity	NPC21469
0.8987	High Similarity	NPC470755
0.8987	High Similarity	NPC255307
0.8974	High Similarity	NPC250315
0.8947	High Similarity	NPC470239
0.8947	High Similarity	NPC470244
0.8904	High Similarity	NPC58956
0.8904	High Similarity	NPC269206
0.8904	High Similarity	NPC295633
0.8875	High Similarity	NPC469910
0.8875	High Similarity	NPC305475
0.8875	High Similarity	NPC475461
0.8861	High Similarity	NPC96259
0.8861	High Similarity	NPC191476
0.8861	High Similarity	NPC141193
0.8861	High Similarity	NPC114979
0.88	High Similarity	NPC123360
0.875	High Similarity	NPC165162
0.8734	High Similarity	NPC59097
0.8718	High Similarity	NPC325031
0.8718	High Similarity	NPC52861
0.8701	High Similarity	NPC89128
0.8684	High Similarity	NPC97516
0.8684	High Similarity	NPC141789
0.8684	High Similarity	NPC476028
0.8684	High Similarity	NPC171204
0.8659	High Similarity	NPC476805
0.8659	High Similarity	NPC476803
0.8659	High Similarity	NPC475819
0.8554	High Similarity	NPC295312
0.8554	High Similarity	NPC474032
0.8553	High Similarity	NPC68819
0.8553	High Similarity	NPC235906
0.8537	High Similarity	NPC160138
0.85	High Similarity	NPC116543
0.8472	Intermediate Similarity	NPC194871
0.8462	Intermediate Similarity	NPC270126
0.8452	Intermediate Similarity	NPC475855
0.8452	Intermediate Similarity	NPC474232
0.8452	Intermediate Similarity	NPC469368
0.8442	Intermediate Similarity	NPC476794
0.8442	Intermediate Similarity	NPC187568
0.8442	Intermediate Similarity	NPC65603
0.8442	Intermediate Similarity	NPC41780
0.8442	Intermediate Similarity	NPC470240
0.8434	Intermediate Similarity	NPC473715
0.8421	Intermediate Similarity	NPC155587
0.8421	Intermediate Similarity	NPC226669
0.8421	Intermediate Similarity	NPC138408
0.8421	Intermediate Similarity	NPC193351
0.8415	Intermediate Similarity	NPC150755
0.8378	Intermediate Similarity	NPC67183
0.8375	Intermediate Similarity	NPC89555
0.8356	Intermediate Similarity	NPC470256
0.8354	Intermediate Similarity	NPC281132
0.8353	Intermediate Similarity	NPC473321
0.8333	Intermediate Similarity	NPC206001
0.8333	Intermediate Similarity	NPC268298
0.8333	Intermediate Similarity	NPC218927
0.8289	Intermediate Similarity	NPC114727
0.8289	Intermediate Similarity	NPC476590
0.8267	Intermediate Similarity	NPC129665
0.8256	Intermediate Similarity	NPC228451
0.8256	Intermediate Similarity	NPC475912
0.8256	Intermediate Similarity	NPC288240
0.8256	Intermediate Similarity	NPC162205
0.8256	Intermediate Similarity	NPC125674
0.8256	Intermediate Similarity	NPC273579
0.8256	Intermediate Similarity	NPC469645
0.8256	Intermediate Similarity	NPC295204
0.8256	Intermediate Similarity	NPC475838
0.8256	Intermediate Similarity	NPC469692
0.825	Intermediate Similarity	NPC141810
0.825	Intermediate Similarity	NPC281949
0.825	Intermediate Similarity	NPC301477
0.825	Intermediate Similarity	NPC25684
0.8235	Intermediate Similarity	NPC473619
0.8235	Intermediate Similarity	NPC476004
0.8235	Intermediate Similarity	NPC474761
0.8235	Intermediate Similarity	NPC144133
0.8235	Intermediate Similarity	NPC179394
0.8235	Intermediate Similarity	NPC129419
0.8228	Intermediate Similarity	NPC178277
0.8228	Intermediate Similarity	NPC617
0.8214	Intermediate Similarity	NPC202672
0.8214	Intermediate Similarity	NPC477302
0.8214	Intermediate Similarity	NPC136879
0.8205	Intermediate Similarity	NPC57744
0.8193	Intermediate Similarity	NPC261721
0.8182	Intermediate Similarity	NPC329852
0.8171	Intermediate Similarity	NPC82297
0.8171	Intermediate Similarity	NPC70424
0.8171	Intermediate Similarity	NPC243618
0.8161	Intermediate Similarity	NPC121825
0.8161	Intermediate Similarity	NPC81386
0.8161	Intermediate Similarity	NPC474035
0.8161	Intermediate Similarity	NPC474247
0.8148	Intermediate Similarity	NPC474252
0.8148	Intermediate Similarity	NPC173609
0.8148	Intermediate Similarity	NPC474291
0.814	Intermediate Similarity	NPC30515
0.8133	Intermediate Similarity	NPC4299
0.8101	Intermediate Similarity	NPC128276
0.8095	Intermediate Similarity	NPC72513
0.8095	Intermediate Similarity	NPC312561
0.8072	Intermediate Similarity	NPC261380
0.8072	Intermediate Similarity	NPC215364
0.8068	Intermediate Similarity	NPC270013
0.8068	Intermediate Similarity	NPC14961
0.8068	Intermediate Similarity	NPC36954
0.8068	Intermediate Similarity	NPC304886
0.8068	Intermediate Similarity	NPC471142
0.8068	Intermediate Similarity	NPC477922
0.8052	Intermediate Similarity	NPC48641
0.8052	Intermediate Similarity	NPC472966
0.8049	Intermediate Similarity	NPC318468
0.8046	Intermediate Similarity	NPC81419
0.8046	Intermediate Similarity	NPC475302
0.8046	Intermediate Similarity	NPC179746
0.8026	Intermediate Similarity	NPC477086
0.8026	Intermediate Similarity	NPC477087
0.8025	Intermediate Similarity	NPC470241
0.8025	Intermediate Similarity	NPC471325
0.8023	Intermediate Similarity	NPC71533
0.8023	Intermediate Similarity	NPC51004
0.8023	Intermediate Similarity	NPC106510
0.8	Intermediate Similarity	NPC101622
0.8	Intermediate Similarity	NPC264227
0.8	Intermediate Similarity	NPC63649
0.8	Intermediate Similarity	NPC475210
0.8	Intermediate Similarity	NPC472965
0.8	Intermediate Similarity	NPC182550
0.8	Intermediate Similarity	NPC19841
0.7978	Intermediate Similarity	NPC477921
0.7978	Intermediate Similarity	NPC279621
0.7978	Intermediate Similarity	NPC476315
0.7978	Intermediate Similarity	NPC230800
0.7976	Intermediate Similarity	NPC284902
0.7976	Intermediate Similarity	NPC469483
0.7975	Intermediate Similarity	NPC474760
0.7955	Intermediate Similarity	NPC57405
0.7955	Intermediate Similarity	NPC474338
0.7955	Intermediate Similarity	NPC303942
0.7952	Intermediate Similarity	NPC472958
0.7952	Intermediate Similarity	NPC472957
0.7952	Intermediate Similarity	NPC295799
0.7952	Intermediate Similarity	NPC156485
0.7931	Intermediate Similarity	NPC261607
0.7931	Intermediate Similarity	NPC184463
0.7931	Intermediate Similarity	NPC12172
0.7931	Intermediate Similarity	NPC300312
0.7931	Intermediate Similarity	NPC111114
0.7931	Intermediate Similarity	NPC208886
0.7927	Intermediate Similarity	NPC85772
0.7922	Intermediate Similarity	NPC477085
0.7907	Intermediate Similarity	NPC307411
0.7907	Intermediate Similarity	NPC50488
0.7907	Intermediate Similarity	NPC212598
0.7907	Intermediate Similarity	NPC474396
0.7901	Intermediate Similarity	NPC302426
0.7901	Intermediate Similarity	NPC233377
0.7901	Intermediate Similarity	NPC276356
0.7889	Intermediate Similarity	NPC474343
0.7882	Intermediate Similarity	NPC237540
0.7875	Intermediate Similarity	NPC192006
0.7875	Intermediate Similarity	NPC472960
0.7867	Intermediate Similarity	NPC218477
0.7857	Intermediate Similarity	NPC132496
0.7857	Intermediate Similarity	NPC1083
0.7857	Intermediate Similarity	NPC231009
0.7857	Intermediate Similarity	NPC107986
0.7857	Intermediate Similarity	NPC82795
0.7857	Intermediate Similarity	NPC103284
0.7857	Intermediate Similarity	NPC473478
0.7857	Intermediate Similarity	NPC223871
0.7857	Intermediate Similarity	NPC125290
0.7857	Intermediate Similarity	NPC283085
0.7857	Intermediate Similarity	NPC473669
0.7857	Intermediate Similarity	NPC66346
0.7857	Intermediate Similarity	NPC286338

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 NPC320630 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1621
0.2-0.3	3818
0.3-0.4	2463
0.4-0.5	689
0.5-0.6	324
0.6-0.7	69
0.7-0.8	23
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7831	Intermediate Similarity	NPD7154	Phase 3
0.7816	Intermediate Similarity	NPD5785	Approved
0.7647	Intermediate Similarity	NPD5363	Approved
0.7619	Intermediate Similarity	NPD5362	Discontinued
0.75	Intermediate Similarity	NPD4269	Approved
0.75	Intermediate Similarity	NPD4270	Approved
0.7473	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4252	Approved
0.7442	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD6698	Approved
0.7416	Intermediate Similarity	NPD46	Approved
0.7356	Intermediate Similarity	NPD5786	Approved
0.7241	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1694	Approved
0.7234	Intermediate Similarity	NPD4225	Approved
0.7229	Intermediate Similarity	NPD4271	Approved
0.7229	Intermediate Similarity	NPD4268	Approved
0.7229	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5369	Approved
0.7159	Intermediate Similarity	NPD4249	Approved
0.7111	Intermediate Similarity	NPD1695	Approved
0.7093	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4250	Approved
0.7079	Intermediate Similarity	NPD4251	Approved
0.7059	Intermediate Similarity	NPD4822	Approved
0.7059	Intermediate Similarity	NPD4819	Approved
0.7059	Intermediate Similarity	NPD4821	Approved
0.7059	Intermediate Similarity	NPD4820	Approved
0.7013	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5331	Approved
0.7011	Intermediate Similarity	NPD5332	Approved
0.6977	Remote Similarity	NPD4790	Discontinued
0.6957	Remote Similarity	NPD7983	Approved
0.6933	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5370	Suspended
0.6905	Remote Similarity	NPD4756	Discovery
0.69	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6435	Approved
0.6897	Remote Similarity	NPD5209	Approved
0.6882	Remote Similarity	NPD5778	Approved
0.6882	Remote Similarity	NPD5779	Approved
0.6875	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD8039	Approved
0.6863	Remote Similarity	NPD6371	Approved
0.6848	Remote Similarity	NPD7838	Discovery
0.6774	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7839	Suspended
0.6667	Remote Similarity	NPD3197	Phase 1
0.6667	Remote Similarity	NPD5368	Approved
0.6635	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7640	Approved
0.6633	Remote Similarity	NPD7639	Approved
0.6625	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6101	Approved
0.6559	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7638	Approved
0.6526	Remote Similarity	NPD6399	Phase 3
0.6505	Remote Similarity	NPD6686	Approved
0.6481	Remote Similarity	NPD7115	Discovery
0.6438	Remote Similarity	NPD3172	Approved
0.6421	Remote Similarity	NPD7637	Suspended
0.6421	Remote Similarity	NPD6411	Approved
0.6413	Remote Similarity	NPD6422	Discontinued
0.6389	Remote Similarity	NPD6927	Phase 3
0.6351	Remote Similarity	NPD3194	Approved
0.6351	Remote Similarity	NPD3195	Phase 2
0.6351	Remote Similarity	NPD3196	Approved
0.6351	Remote Similarity	NPD4266	Approved
0.6333	Remote Similarity	NPD3667	Approved
0.6296	Remote Similarity	NPD7331	Phase 2
0.6289	Remote Similarity	NPD5282	Discontinued
0.6275	Remote Similarity	NPD6647	Phase 2
0.6267	Remote Similarity	NPD342	Phase 1
0.6264	Remote Similarity	NPD6110	Phase 1
0.6262	Remote Similarity	NPD6053	Discontinued
0.6238	Remote Similarity	NPD5344	Discontinued
0.6237	Remote Similarity	NPD6684	Approved
0.6237	Remote Similarity	NPD7521	Approved
0.6237	Remote Similarity	NPD7334	Approved
0.6237	Remote Similarity	NPD3618	Phase 1
0.6237	Remote Similarity	NPD7146	Approved
0.6237	Remote Similarity	NPD6409	Approved
0.6237	Remote Similarity	NPD5330	Approved
0.6203	Remote Similarity	NPD368	Approved
0.6196	Remote Similarity	NPD4786	Approved
0.6196	Remote Similarity	NPD3665	Phase 1
0.6196	Remote Similarity	NPD3133	Approved
0.6196	Remote Similarity	NPD3666	Approved
0.6162	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7748	Approved
0.6111	Remote Similarity	NPD3173	Approved
0.6106	Remote Similarity	NPD8513	Phase 3
0.6106	Remote Similarity	NPD8515	Approved
0.6106	Remote Similarity	NPD8516	Approved
0.6106	Remote Similarity	NPD8517	Approved
0.6105	Remote Similarity	NPD6903	Approved
0.6105	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7902	Approved
0.61	Remote Similarity	NPD6083	Phase 2
0.61	Remote Similarity	NPD6084	Phase 2
0.6098	Remote Similarity	NPD3704	Approved
0.6082	Remote Similarity	NPD7515	Phase 2
0.6064	Remote Similarity	NPD5279	Phase 3
0.6061	Remote Similarity	NPD5695	Phase 3
0.604	Remote Similarity	NPD5696	Approved
0.6019	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7632	Discontinued
0.598	Remote Similarity	NPD6648	Approved
0.5976	Remote Similarity	NPD7341	Phase 2
0.5957	Remote Similarity	NPD1696	Phase 3
0.5949	Remote Similarity	NPD3198	Approved
0.5946	Remote Similarity	NPD28	Approved
0.5946	Remote Similarity	NPD29	Approved
0.5943	Remote Similarity	NPD5697	Approved
0.5938	Remote Similarity	NPD6672	Approved
0.5938	Remote Similarity	NPD5737	Approved
0.5934	Remote Similarity	NPD4695	Discontinued
0.5918	Remote Similarity	NPD6079	Approved
0.5918	Remote Similarity	NPD5693	Phase 1
0.5904	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD4623	Approved
0.5895	Remote Similarity	NPD4519	Discontinued
0.5889	Remote Similarity	NPD3732	Approved
0.5888	Remote Similarity	NPD6881	Approved
0.5888	Remote Similarity	NPD6011	Approved
0.5888	Remote Similarity	NPD6899	Approved
0.5876	Remote Similarity	NPD5328	Approved
0.5872	Remote Similarity	NPD6650	Approved
0.5872	Remote Similarity	NPD6649	Approved
0.5859	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5739	Approved
0.5849	Remote Similarity	NPD6402	Approved
0.5849	Remote Similarity	NPD7128	Approved
0.5849	Remote Similarity	NPD6675	Approved
0.5847	Remote Similarity	NPD8074	Phase 3
0.5842	Remote Similarity	NPD4228	Discovery
0.5833	Remote Similarity	NPD6013	Approved
0.5833	Remote Similarity	NPD6012	Approved
0.5833	Remote Similarity	NPD6014	Approved
0.5833	Remote Similarity	NPD6373	Approved
0.5833	Remote Similarity	NPD6372	Approved
0.5833	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD6109	Phase 1
0.5816	Remote Similarity	NPD5207	Approved
0.58	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.58	Remote Similarity	NPD7900	Approved
0.5794	Remote Similarity	NPD5701	Approved
0.5789	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.578	Remote Similarity	NPD6420	Discontinued
0.578	Remote Similarity	NPD6421	Discontinued
0.578	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.578	Remote Similarity	NPD7102	Approved
0.578	Remote Similarity	NPD7290	Approved
0.578	Remote Similarity	NPD2067	Discontinued
0.578	Remote Similarity	NPD6883	Approved
0.5761	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD5281	Approved
0.5758	Remote Similarity	NPD8035	Phase 2
0.5758	Remote Similarity	NPD5284	Approved
0.5758	Remote Similarity	NPD8034	Phase 2
0.5755	Remote Similarity	NPD5909	Discontinued
0.5753	Remote Similarity	NPD622	Approved
0.5753	Remote Similarity	NPD5343	Approved
0.5745	Remote Similarity	NPD6695	Phase 3
0.5743	Remote Similarity	NPD5210	Approved
0.5743	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD4629	Approved
0.5741	Remote Similarity	NPD7320	Approved
0.573	Remote Similarity	NPD8264	Approved
0.5727	Remote Similarity	NPD6617	Approved
0.5727	Remote Similarity	NPD8130	Phase 1
0.5727	Remote Similarity	NPD6869	Approved
0.5727	Remote Similarity	NPD2204	Approved
0.5727	Remote Similarity	NPD6847	Approved
0.5714	Remote Similarity	NPD6051	Approved
0.5714	Remote Similarity	NPD5211	Phase 2
0.5714	Remote Similarity	NPD4753	Phase 2
0.5714	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD9298	Approved
0.5714	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD6008	Approved
0.57	Remote Similarity	NPD4202	Approved
0.5699	Remote Similarity	NPD857	Phase 3
0.5694	Remote Similarity	NPD4265	Approved
0.5694	Remote Similarity	NPD3174	Discontinued
0.5694	Remote Similarity	NPD4222	Approved
0.5688	Remote Similarity	NPD6413	Approved
0.5686	Remote Similarity	NPD4697	Phase 3
0.5686	Remote Similarity	NPD5221	Approved
0.5686	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD5222	Approved
0.5686	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD3668	Phase 3

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