NPASS Compound

Structure

NPC470256 OpenBabel07101719242D 23 24 0 0 1 0 0 0 0 0999 V2000 6.2239 1.0256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0290 -1.8345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5021 4.4789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6885 2.4943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2518 -0.5883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9320 0.1447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3209 -0.9537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0777 2.0891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7203 3.1248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0401 2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5144 2.9154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4577 -0.3789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2267 1.1003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3237 -0.8789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6511 3.4901 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 0.7453 1.4361 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6483 3.4154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8944 0.4473 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7018 0.7124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9431 4.3710 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6906 0.5633 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 2 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 9 15 2 0 0 0 0 11 18 1 0 0 0 0 12 14 2 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 17 10 1 6 0 0 0 17 19 1 0 0 0 0 18 21 2 0 0 0 0 19 12 1 6 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:	314.19
Volume:	347.915
LogP:	3.992
LogD:	3.705
LogS:	-4.441
# Rotatable Bonds:	0
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.377
Synthetic Accessibility Score:	4.422
Fsp3:	0.5
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:	-4.692
MDCK Permeability:	2.5099103368120268e-05
Pgp-inhibitor:	0.879
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.877
20% Bioavailability (F20%):	0.869
30% Bioavailability (F30%):	0.071

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.179
Plasma Protein Binding (PPB):	89.01805877685547%
Volume Distribution (VD):	0.626
Pgp-substrate:	2.471705913543701%

ADMET: Metabolism

CYP1A2-inhibitor:	0.374
CYP1A2-substrate:	0.422
CYP2C19-inhibitor:	0.86
CYP2C19-substrate:	0.136
CYP2C9-inhibitor:	0.834
CYP2C9-substrate:	0.703
CYP2D6-inhibitor:	0.355
CYP2D6-substrate:	0.31
CYP3A4-inhibitor:	0.677
CYP3A4-substrate:	0.173

ADMET: Excretion

Clearance (CL):	5.031
Half-life (T1/2):	0.392

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.303
Drug-inuced Liver Injury (DILI):	0.208
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.201
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.952
Carcinogencity:	0.062
Eye Corrosion:	0.221
Eye Irritation:	0.184
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC470256

Natural Product ID:	NPC470256
*Common Name:**	Crassocolide O
IUPAC Name:	(3aS,5Z,10E,14E,15aS)-6,10,14-trimethyl-3-methylidene-4,8,9,12,13,15a-hexahydro-3aH-cyclotetradeca[b]furan-2,7-dione
Synonyms:	Crassocolide O
Standard InCHIKey:	MWYQRKSBBTVTOQ-GXHOQLSRSA-N
Standard InCHI:	InChI=1S/C20H26O3/c1-13-6-5-7-14(2)12-19-17(16(4)20(22)23-19)10-9-15(3)18(21)11-8-13/h6,9,12,17,19H,4-5,7-8,10-11H2,1-3H3/b13-6+,14-12+,15-9-/t17-,19-/m0/s1
SMILES:	C/C/1=C[C@@H]2OC(=O)C(=C)[C@@H]2C/C=C(C(=O)CC/C(=C/CC1)/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1923745
PubChem CID:	54764415
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
NPO9909	Sarcophyton crassocaule	Species	Alcyoniidae	Eukaryota	n.a.	formosan soft coral	n.a.	PMID[11141104]
NPO9909	Sarcophyton crassocaule	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067165]
NPO9909	Sarcophyton crassocaule	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125220]
NPO9909	Sarcophyton crassocaule	Species	Alcyoniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[22014827]
NPO9909	Sarcophyton crassocaule	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[458794]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[458794]
NPT1184	Cell Line	Daoy	Homo sapiens	IC50	=	4.5	ug.mL-1	PMID[458794]

☑ 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 NPC470256 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	163
0.1-0.2	1547
0.2-0.3	8535
0.3-0.4	17067
0.4-0.5	8047
0.5-0.6	5106
0.6-0.7	1718
0.7-0.8	446
0.8-0.85	53
0.85-0.9	10
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9531	High Similarity	NPC194871
0.9242	High Similarity	NPC476591
0.9242	High Similarity	NPC88877
0.9206	High Similarity	NPC474658
0.8986	High Similarity	NPC476355
0.8971	High Similarity	NPC163003
0.875	High Similarity	NPC151648
0.8732	High Similarity	NPC123360
0.8714	High Similarity	NPC117746
0.8714	High Similarity	NPC294434
0.8714	High Similarity	NPC15499
0.8714	High Similarity	NPC140287
0.8714	High Similarity	NPC259599
0.863	High Similarity	NPC270126
0.8571	High Similarity	NPC295633
0.8571	High Similarity	NPC58956
0.8571	High Similarity	NPC269206
0.8507	High Similarity	NPC248125
0.8493	Intermediate Similarity	NPC108816
0.8493	Intermediate Similarity	NPC93763
0.8451	Intermediate Similarity	NPC476590
0.8451	Intermediate Similarity	NPC114727
0.8382	Intermediate Similarity	NPC203335
0.8378	Intermediate Similarity	NPC178277
0.8358	Intermediate Similarity	NPC470688
0.8356	Intermediate Similarity	NPC476028
0.8356	Intermediate Similarity	NPC41780
0.8356	Intermediate Similarity	NPC171204
0.8356	Intermediate Similarity	NPC141789
0.8356	Intermediate Similarity	NPC7563
0.8356	Intermediate Similarity	NPC320630
0.8356	Intermediate Similarity	NPC187568
0.8356	Intermediate Similarity	NPC57744
0.8356	Intermediate Similarity	NPC116177
0.8356	Intermediate Similarity	NPC97516
0.8356	Intermediate Similarity	NPC65603
0.8333	Intermediate Similarity	NPC193351
0.8333	Intermediate Similarity	NPC226669
0.8333	Intermediate Similarity	NPC155587
0.8333	Intermediate Similarity	NPC138408
0.8289	Intermediate Similarity	NPC173609
0.8267	Intermediate Similarity	NPC281132
0.8243	Intermediate Similarity	NPC267231
0.8243	Intermediate Similarity	NPC128276
0.8219	Intermediate Similarity	NPC235906
0.8219	Intermediate Similarity	NPC68819
0.8194	Intermediate Similarity	NPC474758
0.8158	Intermediate Similarity	NPC281949
0.8158	Intermediate Similarity	NPC25684
0.8158	Intermediate Similarity	NPC301477
0.8158	Intermediate Similarity	NPC471325
0.8133	Intermediate Similarity	NPC264227
0.8133	Intermediate Similarity	NPC472965
0.8133	Intermediate Similarity	NPC63649
0.8116	Intermediate Similarity	NPC21998
0.8108	Intermediate Similarity	NPC476794
0.8108	Intermediate Similarity	NPC470240
0.8082	Intermediate Similarity	NPC329852
0.8026	Intermediate Similarity	NPC302426
0.8	Intermediate Similarity	NPC196653
0.8	Intermediate Similarity	NPC471465
0.8	Intermediate Similarity	NPC218477
0.7949	Intermediate Similarity	NPC169575
0.7949	Intermediate Similarity	NPC40746
0.7949	Intermediate Similarity	NPC318468
0.7949	Intermediate Similarity	NPC116543
0.7922	Intermediate Similarity	NPC141810
0.7922	Intermediate Similarity	NPC42470
0.7917	Intermediate Similarity	NPC129665
0.7895	Intermediate Similarity	NPC98557
0.7895	Intermediate Similarity	NPC167881
0.7895	Intermediate Similarity	NPC617
0.7879	Intermediate Similarity	NPC286189
0.7875	Intermediate Similarity	NPC107787
0.7867	Intermediate Similarity	NPC10572
0.7857	Intermediate Similarity	NPC472266
0.7848	Intermediate Similarity	NPC115786
0.7808	Intermediate Similarity	NPC287878
0.7794	Intermediate Similarity	NPC474774
0.7794	Intermediate Similarity	NPC210303
0.7794	Intermediate Similarity	NPC155849
0.7794	Intermediate Similarity	NPC179087
0.7794	Intermediate Similarity	NPC44343
0.7792	Intermediate Similarity	NPC69271
0.7792	Intermediate Similarity	NPC223904
0.7792	Intermediate Similarity	NPC74673
0.7778	Intermediate Similarity	NPC469660
0.7763	Intermediate Similarity	NPC299235
0.7763	Intermediate Similarity	NPC253749
0.7763	Intermediate Similarity	NPC472960
0.7761	Intermediate Similarity	NPC79756
0.775	Intermediate Similarity	NPC470755
0.775	Intermediate Similarity	NPC215364
0.775	Intermediate Similarity	NPC78089
0.7746	Intermediate Similarity	NPC276290
0.7733	Intermediate Similarity	NPC27205
0.7722	Intermediate Similarity	NPC475947
0.7722	Intermediate Similarity	NPC250315
0.7722	Intermediate Similarity	NPC131669
0.7722	Intermediate Similarity	NPC473390
0.7722	Intermediate Similarity	NPC39588
0.7722	Intermediate Similarity	NPC170286
0.7722	Intermediate Similarity	NPC59097
0.7692	Intermediate Similarity	NPC325031
0.7692	Intermediate Similarity	NPC10276
0.7692	Intermediate Similarity	NPC35089
0.7692	Intermediate Similarity	NPC275507
0.7692	Intermediate Similarity	NPC24417
0.7681	Intermediate Similarity	NPC34883
0.7671	Intermediate Similarity	NPC257618
0.7671	Intermediate Similarity	NPC84038
0.7671	Intermediate Similarity	NPC186531
0.7662	Intermediate Similarity	NPC471299
0.7662	Intermediate Similarity	NPC473981
0.7662	Intermediate Similarity	NPC470244
0.7662	Intermediate Similarity	NPC473980
0.7662	Intermediate Similarity	NPC470239
0.7662	Intermediate Similarity	NPC182550
0.7654	Intermediate Similarity	NPC38576
0.7654	Intermediate Similarity	NPC284902
0.7654	Intermediate Similarity	NPC305475
0.7654	Intermediate Similarity	NPC475461
0.7654	Intermediate Similarity	NPC279859
0.7639	Intermediate Similarity	NPC151481
0.7639	Intermediate Similarity	NPC476059
0.7639	Intermediate Similarity	NPC265574
0.7639	Intermediate Similarity	NPC473603
0.7639	Intermediate Similarity	NPC470693
0.7632	Intermediate Similarity	NPC474760
0.7625	Intermediate Similarity	NPC158756
0.7625	Intermediate Similarity	NPC476804
0.7625	Intermediate Similarity	NPC96259
0.7625	Intermediate Similarity	NPC141193
0.76	Intermediate Similarity	NPC244166
0.7595	Intermediate Similarity	NPC475690
0.7595	Intermediate Similarity	NPC229825
0.7571	Intermediate Similarity	NPC131174
0.7571	Intermediate Similarity	NPC133904
0.7571	Intermediate Similarity	NPC182794
0.7568	Intermediate Similarity	NPC474705
0.7568	Intermediate Similarity	NPC472956
0.7564	Intermediate Similarity	NPC276356
0.7561	Intermediate Similarity	NPC160138
0.7561	Intermediate Similarity	NPC475703
0.7536	Intermediate Similarity	NPC217940
0.7536	Intermediate Similarity	NPC68110
0.7534	Intermediate Similarity	NPC318766
0.7534	Intermediate Similarity	NPC67183
0.7532	Intermediate Similarity	NPC471220
0.7532	Intermediate Similarity	NPC475699
0.7531	Intermediate Similarity	NPC21469
0.7531	Intermediate Similarity	NPC255307
0.7531	Intermediate Similarity	NPC155873
0.7531	Intermediate Similarity	NPC161957
0.7531	Intermediate Similarity	NPC21471
0.7531	Intermediate Similarity	NPC165162
0.7531	Intermediate Similarity	NPC33570
0.75	Intermediate Similarity	NPC179394
0.75	Intermediate Similarity	NPC474703
0.75	Intermediate Similarity	NPC472967
0.75	Intermediate Similarity	NPC301207
0.75	Intermediate Similarity	NPC16488
0.75	Intermediate Similarity	NPC272814
0.75	Intermediate Similarity	NPC144133
0.75	Intermediate Similarity	NPC215294
0.75	Intermediate Similarity	NPC19241
0.75	Intermediate Similarity	NPC266159
0.75	Intermediate Similarity	NPC193198
0.747	Intermediate Similarity	NPC475819
0.747	Intermediate Similarity	NPC476805
0.7468	Intermediate Similarity	NPC150502
0.7465	Intermediate Similarity	NPC191233
0.7439	Intermediate Similarity	NPC150755
0.7439	Intermediate Similarity	NPC50637
0.7439	Intermediate Similarity	NPC261721
0.7439	Intermediate Similarity	NPC469910
0.7436	Intermediate Similarity	NPC99651
0.7436	Intermediate Similarity	NPC469690
0.7432	Intermediate Similarity	NPC319163
0.7432	Intermediate Similarity	NPC67076
0.7407	Intermediate Similarity	NPC159635
0.7407	Intermediate Similarity	NPC191476
0.7407	Intermediate Similarity	NPC114979
0.7407	Intermediate Similarity	NPC38569
0.7407	Intermediate Similarity	NPC163615
0.7403	Intermediate Similarity	NPC15975
0.7403	Intermediate Similarity	NPC51809
0.7403	Intermediate Similarity	NPC474818
0.7403	Intermediate Similarity	NPC195785
0.7403	Intermediate Similarity	NPC49302
0.7403	Intermediate Similarity	NPC125365
0.7403	Intermediate Similarity	NPC471225
0.7403	Intermediate Similarity	NPC176329
0.7397	Intermediate Similarity	NPC296522
0.7397	Intermediate Similarity	NPC144511
0.7397	Intermediate Similarity	NPC475982
0.7381	Intermediate Similarity	NPC166919
0.7381	Intermediate Similarity	NPC295312
0.7381	Intermediate Similarity	NPC268298
0.7375	Intermediate Similarity	NPC474959

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 NPC470256 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	2085
0.2-0.3	4447
0.3-0.4	1783
0.4-0.5	463
0.5-0.6	165
0.6-0.7	45
0.7-0.8	3
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
0.7595	Intermediate Similarity	NPD5209	Approved
0.7571	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1694	Approved
0.7188	Intermediate Similarity	NPD6927	Phase 3
0.7108	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5785	Approved
0.6782	Remote Similarity	NPD1695	Approved
0.6778	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5363	Approved
0.6559	Remote Similarity	NPD4225	Approved
0.6517	Remote Similarity	NPD6698	Approved
0.6517	Remote Similarity	NPD46	Approved
0.6512	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4252	Approved
0.65	Remote Similarity	NPD8039	Approved
0.6471	Remote Similarity	NPD7154	Phase 3
0.6462	Remote Similarity	NPD5343	Approved
0.6395	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD4269	Approved
0.6353	Remote Similarity	NPD4270	Approved
0.6341	Remote Similarity	NPD4756	Discovery
0.6333	Remote Similarity	NPD7838	Discovery
0.6301	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD5362	Discontinued
0.6267	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD4271	Approved
0.6265	Remote Similarity	NPD4268	Approved
0.6265	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6409	Approved
0.625	Remote Similarity	NPD5330	Approved
0.625	Remote Similarity	NPD4249	Approved
0.625	Remote Similarity	NPD7521	Approved
0.625	Remote Similarity	NPD6684	Approved
0.625	Remote Similarity	NPD5786	Approved
0.625	Remote Similarity	NPD7334	Approved
0.625	Remote Similarity	NPD7146	Approved
0.6235	Remote Similarity	NPD5369	Approved
0.6211	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4250	Approved
0.618	Remote Similarity	NPD4251	Approved
0.6118	Remote Similarity	NPD4820	Approved
0.6118	Remote Similarity	NPD4819	Approved
0.6118	Remote Similarity	NPD4822	Approved
0.6118	Remote Similarity	NPD4821	Approved
0.6111	Remote Similarity	NPD6903	Approved
0.6111	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD1452	Discontinued
0.6092	Remote Similarity	NPD5332	Approved
0.6092	Remote Similarity	NPD5331	Approved
0.6078	Remote Similarity	NPD6371	Approved
0.6047	Remote Similarity	NPD4790	Discontinued
0.6044	Remote Similarity	NPD5370	Suspended
0.6042	Remote Similarity	NPD7638	Approved
0.6	Remote Similarity	NPD6096	Approved
0.6	Remote Similarity	NPD6097	Approved
0.5979	Remote Similarity	NPD7639	Approved
0.5979	Remote Similarity	NPD7640	Approved
0.5977	Remote Similarity	NPD6435	Approved
0.5934	Remote Similarity	NPD6672	Approved
0.5934	Remote Similarity	NPD5737	Approved
0.5915	Remote Similarity	NPD9298	Approved
0.5914	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD5693	Phase 1
0.5909	Remote Similarity	NPD3174	Discontinued
0.5909	Remote Similarity	NPD6110	Phase 1
0.589	Remote Similarity	NPD8779	Phase 3
0.5865	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD6399	Phase 3
0.5823	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD6109	Phase 1
0.5806	Remote Similarity	NPD5207	Approved
0.58	Remote Similarity	NPD6647	Phase 2
0.5789	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD7900	Approved
0.5789	Remote Similarity	NPD5282	Discontinued
0.5747	Remote Similarity	NPD5368	Approved
0.5745	Remote Similarity	NPD7637	Suspended
0.5745	Remote Similarity	NPD7983	Approved
0.5741	Remote Similarity	NPD7115	Discovery
0.5729	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD6686	Approved
0.5714	Remote Similarity	NPD29	Approved
0.5714	Remote Similarity	NPD28	Approved
0.5714	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6422	Discontinued
0.5699	Remote Similarity	NPD6051	Approved
0.5696	Remote Similarity	NPD7331	Phase 2
0.5686	Remote Similarity	NPD6008	Approved
0.5684	Remote Similarity	NPD5778	Approved
0.5684	Remote Similarity	NPD5779	Approved
0.5672	Remote Similarity	NPD4222	Approved
0.5657	Remote Similarity	NPD6648	Approved
0.5652	Remote Similarity	NPD3173	Approved
0.5652	Remote Similarity	NPD4220	Pre-registration
0.5652	Remote Similarity	NPD3573	Approved
0.5641	Remote Similarity	NPD3197	Phase 1
0.5625	Remote Similarity	NPD7748	Approved
0.5625	Remote Similarity	NPD6001	Approved
0.5619	Remote Similarity	NPD2067	Discontinued
0.5612	Remote Similarity	NPD7902	Approved
0.561	Remote Similarity	NPD4691	Approved
0.56	Remote Similarity	NPD5344	Discontinued

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