NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	614.26
Volume:	592.874
LogP:	3.097
LogD:	1.531
LogS:	-5.438
# Rotatable Bonds:	9
TPSA:	149.93
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.192
Synthetic Accessibility Score:	6.326
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.203
MDCK Permeability:	2.26E-05
Pgp-inhibitor:	0.861
Pgp-substrate:	0
Human Intestinal Absorption (HIA):	0.074
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.845

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088
Plasma Protein Binding (PPB):	94.97%
Volume Distribution (VD):	1.166
Pgp-substrate:	3.04%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.939
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.907
CYP2C9-inhibitor:	0.087
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.232
CYP3A4-inhibitor:	0.183
CYP3A4-substrate:	0.174

ADMET: Excretion

Clearance (CL):	2.346
Half-life (T1/2):	0.065

ADMET: Toxicity

hERG Blockers:	0.422
Human Hepatotoxicity (H-HT):	0.949
Drug-inuced Liver Injury (DILI):	0.594
AMES Toxicity:	0.329
Rat Oral Acute Toxicity:	0.864
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.987
Carcinogencity:	0.822
Eye Corrosion:	0.961
Eye Irritation:	0.649
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC478129

Natural Product ID:	NPC478129
*Common Name:**	WYJAHVSVZYBJTI-JEBIPZLNSA-L
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WYJAHVSVZYBJTI-JEBIPZLNSA-L
Standard InCHI:	InChI=1S/C30H48O9S2.2Na/c1-19(2)15-21(31)16-20(3)22-9-11-28(6)24-8-7-23-26(4,18-38-40(32,33)34)25(39-41(35,36)37)10-12-29(23)17-30(24,29)14-13-27(22,28)5;;/h15,20,22-25H,7-14,16-18H2,1-6H3,(H,32,33,34)(H,35,36,37);;/q;2*+1/p-2/t20-,22-,23+,24+,25+,26+,27-,28+,29-,30+;;/m1../s1
SMILES:	CC(=CC(=O)C[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CC[C@@H]([C@@]2(C)COS(=O)(=O)[O-])OS(=O)(=O)[O-])C)C)C.[Na+].[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446521
PubChem CID:	25058092
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO33593	Tydemania expeditionis	Species		Eukaryota	n.a.	depths of 720 m at Herald Pass, Kadavu Province, Fiji (1846.370' S, 17827.746' E)	n.a.	PMID[18763828]
NPO52	Tydemania expeditionis	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158167]
NPO52	Tydemania expeditionis	Species	Udoteaceae	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	13
Others	1

Activity Type	# Activity
Cell Line	10
NON-MOLECULAR	2
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	31000.0	nM	PMID[557041]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	31000.0	nM	PMID[557041]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	31000.0	nM	PMID[557041]
NPT2155	Cell Line	SHP77	Homo sapiens	IC50	=	31000.0	nM	PMID[557041]
NPT937	Cell Line	NCI-H446	Homo sapiens	IC50	=	31000.0	nM	PMID[557041]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	31000.0	nM	PMID[557041]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	31000.0	nM	PMID[557041]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	IC50	=	31000.0	nM	PMID[557041]
NPT1900	Cell Line	DU-4475	Homo sapiens	IC50	=	31000.0	nM	PMID[557041]
NPT457	Cell Line	BT-549	Homo sapiens	IC50	=	31000.0	nM	PMID[557041]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	31000.0	nM	PMID[557041]
NPT3927	Organism	Rotifers	Rotifera	Activity	=	9.0	%	PMID[557041]
NPT2	Others	Unspecified		IC50	=	39000.0	nM	PMID[557042]

☑ 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 NPC478129 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	242
0.1-0.2	1659
0.2-0.3	7002
0.3-0.4	16068
0.4-0.5	6844
0.5-0.6	6155
0.6-0.7	4102
0.7-0.8	604
0.8-0.85	12
0.85-0.9	3
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.875	High Similarity	NPC478127
0.8696	High Similarity	NPC475255
0.8495	Intermediate Similarity	NPC12722
0.8409	Intermediate Similarity	NPC328351
0.8372	Intermediate Similarity	NPC478128
0.837	Intermediate Similarity	NPC1015
0.837	Intermediate Similarity	NPC31985
0.828	Intermediate Similarity	NPC126993
0.8222	Intermediate Similarity	NPC25833
0.8191	Intermediate Similarity	NPC272746
0.8152	Intermediate Similarity	NPC475740
0.8132	Intermediate Similarity	NPC76518
0.8132	Intermediate Similarity	NPC470574
0.81	Intermediate Similarity	NPC312900
0.8085	Intermediate Similarity	NPC85173
0.8065	Intermediate Similarity	NPC292491
0.8065	Intermediate Similarity	NPC328539
0.8065	Intermediate Similarity	NPC310752
0.8065	Intermediate Similarity	NPC193360
0.8065	Intermediate Similarity	NPC471722
0.8043	Intermediate Similarity	NPC478094
0.8043	Intermediate Similarity	NPC72133
0.8043	Intermediate Similarity	NPC474778
0.8043	Intermediate Similarity	NPC474733
0.8043	Intermediate Similarity	NPC145879
0.8043	Intermediate Similarity	NPC474732
0.8043	Intermediate Similarity	NPC31564
0.8041	Intermediate Similarity	NPC327788
0.8022	Intermediate Similarity	NPC214043
0.8022	Intermediate Similarity	NPC85774
0.8021	Intermediate Similarity	NPC111015
0.8021	Intermediate Similarity	NPC245972
0.8021	Intermediate Similarity	NPC196485
0.8	Intermediate Similarity	NPC185936
0.8	Intermediate Similarity	NPC168027
0.8	Intermediate Similarity	NPC473998
0.7979	Intermediate Similarity	NPC475921
0.7979	Intermediate Similarity	NPC474704
0.7979	Intermediate Similarity	NPC275740
0.7979	Intermediate Similarity	NPC309603
0.7979	Intermediate Similarity	NPC473999
0.7979	Intermediate Similarity	NPC86319
0.7957	Intermediate Similarity	NPC89747
0.7957	Intermediate Similarity	NPC141292
0.7957	Intermediate Similarity	NPC58063
0.7957	Intermediate Similarity	NPC478104
0.7955	Intermediate Similarity	NPC475337
0.7938	Intermediate Similarity	NPC476174
0.7935	Intermediate Similarity	NPC22133
0.7895	Intermediate Similarity	NPC48010
0.7895	Intermediate Similarity	NPC191684
0.7895	Intermediate Similarity	NPC475965
0.7895	Intermediate Similarity	NPC474842
0.7889	Intermediate Similarity	NPC473534
0.7879	Intermediate Similarity	NPC252295
0.7872	Intermediate Similarity	NPC131470
0.7872	Intermediate Similarity	NPC474677
0.7872	Intermediate Similarity	NPC143767
0.7843	Intermediate Similarity	NPC72255
0.7835	Intermediate Similarity	NPC473280
0.7835	Intermediate Similarity	NPC471078
0.7835	Intermediate Similarity	NPC473435
0.7835	Intermediate Similarity	NPC474690
0.7835	Intermediate Similarity	NPC8993
0.7835	Intermediate Similarity	NPC473431
0.7835	Intermediate Similarity	NPC209662
0.7826	Intermediate Similarity	NPC469878
0.7826	Intermediate Similarity	NPC473246
0.7826	Intermediate Similarity	NPC221758
0.7826	Intermediate Similarity	NPC59453
0.7826	Intermediate Similarity	NPC478102
0.7812	Intermediate Similarity	NPC475806
0.7812	Intermediate Similarity	NPC155304
0.7802	Intermediate Similarity	NPC163236
0.7789	Intermediate Similarity	NPC268406
0.7789	Intermediate Similarity	NPC186688
0.7789	Intermediate Similarity	NPC271974
0.7789	Intermediate Similarity	NPC474245
0.7789	Intermediate Similarity	NPC122116
0.7789	Intermediate Similarity	NPC26959
0.7789	Intermediate Similarity	NPC247312
0.7789	Intermediate Similarity	NPC477943
0.7789	Intermediate Similarity	NPC128496
0.7789	Intermediate Similarity	NPC32830
0.7789	Intermediate Similarity	NPC119416
0.7778	Intermediate Similarity	NPC18509
0.7778	Intermediate Similarity	NPC156546
0.7778	Intermediate Similarity	NPC108078
0.7766	Intermediate Similarity	NPC93778
0.7766	Intermediate Similarity	NPC474684
0.7766	Intermediate Similarity	NPC142361
0.7766	Intermediate Similarity	NPC90652
0.7755	Intermediate Similarity	NPC88310
0.7755	Intermediate Similarity	NPC180950
0.7755	Intermediate Similarity	NPC271195
0.7755	Intermediate Similarity	NPC473170
0.7742	Intermediate Similarity	NPC197823
0.7742	Intermediate Similarity	NPC469948
0.7732	Intermediate Similarity	NPC69454
0.7732	Intermediate Similarity	NPC474185
0.7732	Intermediate Similarity	NPC476304
0.7732	Intermediate Similarity	NPC472930
0.7723	Intermediate Similarity	NPC476897
0.7717	Intermediate Similarity	NPC139206
0.7717	Intermediate Similarity	NPC470047
0.7717	Intermediate Similarity	NPC470046
0.7717	Intermediate Similarity	NPC472743
0.7717	Intermediate Similarity	NPC475726
0.7708	Intermediate Similarity	NPC183283
0.7708	Intermediate Similarity	NPC471896
0.77	Intermediate Similarity	NPC191565
0.7692	Intermediate Similarity	NPC473217
0.7684	Intermediate Similarity	NPC472802
0.7684	Intermediate Similarity	NPC80335
0.7684	Intermediate Similarity	NPC471724
0.7684	Intermediate Similarity	NPC470417
0.7684	Intermediate Similarity	NPC146937
0.7677	Intermediate Similarity	NPC160056
0.7677	Intermediate Similarity	NPC122324
0.7677	Intermediate Similarity	NPC151725
0.7677	Intermediate Similarity	NPC106425
0.7677	Intermediate Similarity	NPC114743
0.7677	Intermediate Similarity	NPC471153
0.7677	Intermediate Similarity	NPC307164
0.7677	Intermediate Similarity	NPC192428
0.7677	Intermediate Similarity	NPC29152
0.7677	Intermediate Similarity	NPC249954
0.7677	Intermediate Similarity	NPC195366
0.7667	Intermediate Similarity	NPC215843
0.766	Intermediate Similarity	NPC118648
0.766	Intermediate Similarity	NPC222613
0.766	Intermediate Similarity	NPC158393
0.766	Intermediate Similarity	NPC213412
0.766	Intermediate Similarity	NPC195640
0.766	Intermediate Similarity	NPC51014
0.766	Intermediate Similarity	NPC471737
0.766	Intermediate Similarity	NPC475022
0.766	Intermediate Similarity	NPC94755
0.7653	Intermediate Similarity	NPC476186
0.7653	Intermediate Similarity	NPC299100
0.7653	Intermediate Similarity	NPC166906
0.7653	Intermediate Similarity	NPC124207
0.7647	Intermediate Similarity	NPC22388
0.7647	Intermediate Similarity	NPC271980
0.7647	Intermediate Similarity	NPC193934
0.7634	Intermediate Similarity	NPC472265
0.7634	Intermediate Similarity	NPC58841
0.7634	Intermediate Similarity	NPC161423
0.7634	Intermediate Similarity	NPC227064
0.7634	Intermediate Similarity	NPC82902
0.7634	Intermediate Similarity	NPC475745
0.7634	Intermediate Similarity	NPC237712
0.7634	Intermediate Similarity	NPC474482
0.7634	Intermediate Similarity	NPC329043
0.7634	Intermediate Similarity	NPC321187
0.7629	Intermediate Similarity	NPC233455
0.7629	Intermediate Similarity	NPC4036
0.7629	Intermediate Similarity	NPC233116
0.7629	Intermediate Similarity	NPC110923
0.7629	Intermediate Similarity	NPC65120
0.7629	Intermediate Similarity	NPC145067
0.7629	Intermediate Similarity	NPC74296
0.7629	Intermediate Similarity	NPC86266
0.7629	Intermediate Similarity	NPC189520
0.7629	Intermediate Similarity	NPC158030
0.7629	Intermediate Similarity	NPC212301
0.7629	Intermediate Similarity	NPC63748
0.7629	Intermediate Similarity	NPC110657
0.7629	Intermediate Similarity	NPC131872
0.7624	Intermediate Similarity	NPC144956
0.7624	Intermediate Similarity	NPC154072
0.7624	Intermediate Similarity	NPC470906
0.7614	Intermediate Similarity	NPC255650
0.7609	Intermediate Similarity	NPC151519
0.7609	Intermediate Similarity	NPC477858
0.7604	Intermediate Similarity	NPC77263
0.7604	Intermediate Similarity	NPC250592
0.7604	Intermediate Similarity	NPC229871
0.7604	Intermediate Similarity	NPC310010
0.7604	Intermediate Similarity	NPC326627
0.7604	Intermediate Similarity	NPC469319
0.76	Intermediate Similarity	NPC151488
0.76	Intermediate Similarity	NPC110937
0.76	Intermediate Similarity	NPC190554
0.76	Intermediate Similarity	NPC23680
0.76	Intermediate Similarity	NPC474938
0.76	Intermediate Similarity	NPC474785
0.7579	Intermediate Similarity	NPC187376
0.7579	Intermediate Similarity	NPC241875
0.7579	Intermediate Similarity	NPC469314
0.7579	Intermediate Similarity	NPC269360
0.7579	Intermediate Similarity	NPC174619
0.7579	Intermediate Similarity	NPC475313
0.7579	Intermediate Similarity	NPC469317
0.7579	Intermediate Similarity	NPC264005
0.7579	Intermediate Similarity	NPC317590
0.7579	Intermediate Similarity	NPC159046
0.7579	Intermediate Similarity	NPC233836
0.7576	Intermediate Similarity	NPC266431
0.7576	Intermediate Similarity	NPC33473

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 NPC478129 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1875
0.2-0.3	4464
0.3-0.4	1921
0.4-0.5	331
0.5-0.6	137
0.6-0.7	174
0.7-0.8	65
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
0.8222	Intermediate Similarity	NPD3668	Phase 3
0.8172	Intermediate Similarity	NPD5328	Approved
0.8043	Intermediate Similarity	NPD3618	Phase 1
0.8	Intermediate Similarity	NPD6079	Approved
0.7826	Intermediate Similarity	NPD4786	Approved
0.7778	Intermediate Similarity	NPD4755	Approved
0.7755	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD4202	Approved
0.7684	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD6672	Approved
0.7684	Intermediate Similarity	NPD5737	Approved
0.7677	Intermediate Similarity	NPD5222	Approved
0.7677	Intermediate Similarity	NPD4697	Phase 3
0.7677	Intermediate Similarity	NPD5221	Approved
0.7677	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD5330	Approved
0.766	Intermediate Similarity	NPD7146	Approved
0.766	Intermediate Similarity	NPD6409	Approved
0.766	Intermediate Similarity	NPD7334	Approved
0.766	Intermediate Similarity	NPD6684	Approved
0.766	Intermediate Similarity	NPD7521	Approved
0.7634	Intermediate Similarity	NPD3666	Approved
0.7634	Intermediate Similarity	NPD3665	Phase 1
0.7634	Intermediate Similarity	NPD3133	Approved
0.7629	Intermediate Similarity	NPD7515	Phase 2
0.7624	Intermediate Similarity	NPD5286	Approved
0.7624	Intermediate Similarity	NPD4696	Approved
0.7624	Intermediate Similarity	NPD5285	Approved
0.7624	Intermediate Similarity	NPD4700	Approved
0.7609	Intermediate Similarity	NPD3667	Approved
0.7604	Intermediate Similarity	NPD4753	Phase 2
0.76	Intermediate Similarity	NPD5173	Approved
0.75	Intermediate Similarity	NPD6903	Approved
0.7476	Intermediate Similarity	NPD5211	Phase 2
0.7476	Intermediate Similarity	NPD5225	Approved
0.7476	Intermediate Similarity	NPD5224	Approved
0.7476	Intermediate Similarity	NPD5226	Approved
0.7476	Intermediate Similarity	NPD4633	Approved
0.7475	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7900	Approved
0.7475	Intermediate Similarity	NPD7748	Approved
0.7429	Intermediate Similarity	NPD4768	Approved
0.7429	Intermediate Similarity	NPD5739	Approved
0.7429	Intermediate Similarity	NPD6675	Approved
0.7429	Intermediate Similarity	NPD4767	Approved
0.7429	Intermediate Similarity	NPD7128	Approved
0.7429	Intermediate Similarity	NPD6402	Approved
0.7419	Intermediate Similarity	NPD4223	Phase 3
0.7419	Intermediate Similarity	NPD4221	Approved
0.7404	Intermediate Similarity	NPD5175	Approved
0.7404	Intermediate Similarity	NPD5174	Approved
0.7404	Intermediate Similarity	NPD4754	Approved
0.7391	Intermediate Similarity	NPD7525	Registered
0.7383	Intermediate Similarity	NPD6373	Approved
0.7383	Intermediate Similarity	NPD6372	Approved
0.7379	Intermediate Similarity	NPD5223	Approved
0.7374	Intermediate Similarity	NPD6399	Phase 3
0.7368	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5329	Approved
0.7356	Intermediate Similarity	NPD4747	Approved
0.7333	Intermediate Similarity	NPD5141	Approved
0.73	Intermediate Similarity	NPD6001	Approved
0.7292	Intermediate Similarity	NPD5279	Phase 3
0.7292	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7320	Approved
0.729	Intermediate Similarity	NPD4730	Approved
0.729	Intermediate Similarity	NPD6899	Approved
0.729	Intermediate Similarity	NPD6881	Approved
0.729	Intermediate Similarity	NPD4729	Approved
0.7264	Intermediate Similarity	NPD6008	Approved
0.7263	Intermediate Similarity	NPD4197	Approved
0.7255	Intermediate Similarity	NPD7902	Approved
0.7255	Intermediate Similarity	NPD6083	Phase 2
0.7255	Intermediate Similarity	NPD6084	Phase 2
0.7248	Intermediate Similarity	NPD6650	Approved
0.7248	Intermediate Similarity	NPD6649	Approved
0.7245	Intermediate Similarity	NPD6904	Approved
0.7245	Intermediate Similarity	NPD6080	Approved
0.7245	Intermediate Similarity	NPD6673	Approved
0.7241	Intermediate Similarity	NPD4137	Phase 3
0.7228	Intermediate Similarity	NPD5210	Approved
0.7228	Intermediate Similarity	NPD4629	Approved
0.7196	Intermediate Similarity	NPD5701	Approved
0.7196	Intermediate Similarity	NPD5697	Approved
0.7184	Intermediate Similarity	NPD7638	Approved
0.7182	Intermediate Similarity	NPD8297	Approved
0.7182	Intermediate Similarity	NPD6882	Approved
0.7159	Intermediate Similarity	NPD4691	Approved
0.7158	Intermediate Similarity	NPD4788	Approved
0.7156	Intermediate Similarity	NPD6883	Approved
0.7156	Intermediate Similarity	NPD5247	Approved
0.7156	Intermediate Similarity	NPD5249	Phase 3
0.7156	Intermediate Similarity	NPD5248	Approved
0.7156	Intermediate Similarity	NPD7290	Approved
0.7156	Intermediate Similarity	NPD5251	Approved
0.7156	Intermediate Similarity	NPD7102	Approved
0.7156	Intermediate Similarity	NPD5250	Approved
0.713	Intermediate Similarity	NPD5128	Approved
0.7115	Intermediate Similarity	NPD7639	Approved
0.7115	Intermediate Similarity	NPD7640	Approved
0.7113	Intermediate Similarity	NPD4690	Approved
0.7113	Intermediate Similarity	NPD5205	Approved
0.7113	Intermediate Similarity	NPD4689	Approved
0.7113	Intermediate Similarity	NPD4688	Approved
0.7113	Intermediate Similarity	NPD4138	Approved
0.7113	Intermediate Similarity	NPD4693	Phase 3
0.7111	Intermediate Similarity	NPD5733	Approved
0.71	Intermediate Similarity	NPD8035	Phase 2
0.71	Intermediate Similarity	NPD8034	Phase 2
0.7091	Intermediate Similarity	NPD6617	Approved
0.7091	Intermediate Similarity	NPD8130	Phase 1
0.7091	Intermediate Similarity	NPD6847	Approved
0.7091	Intermediate Similarity	NPD6869	Approved
0.7091	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6012	Approved
0.7064	Intermediate Similarity	NPD6013	Approved
0.7064	Intermediate Similarity	NPD6014	Approved
0.7059	Intermediate Similarity	NPD5695	Phase 3
0.7019	Intermediate Similarity	NPD5696	Approved
0.7	Intermediate Similarity	NPD4634	Approved
0.7	Intermediate Similarity	NPD5135	Approved
0.7	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD3617	Approved
0.6972	Remote Similarity	NPD5168	Approved
0.6972	Remote Similarity	NPD6011	Approved
0.697	Remote Similarity	NPD5208	Approved
0.6939	Remote Similarity	NPD4694	Approved
0.6939	Remote Similarity	NPD5690	Phase 2
0.6939	Remote Similarity	NPD6098	Approved
0.6939	Remote Similarity	NPD5280	Approved
0.6937	Remote Similarity	NPD5215	Approved
0.6937	Remote Similarity	NPD5216	Approved
0.6937	Remote Similarity	NPD5217	Approved
0.6931	Remote Similarity	NPD5693	Phase 1
0.6931	Remote Similarity	NPD6050	Approved
0.693	Remote Similarity	NPD7115	Discovery
0.6923	Remote Similarity	NPD4058	Approved
0.6923	Remote Similarity	NPD4687	Approved
0.6889	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5276	Approved
0.6889	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD3573	Approved
0.6848	Remote Similarity	NPD7339	Approved
0.6848	Remote Similarity	NPD6942	Approved
0.6847	Remote Similarity	NPD5169	Approved
0.6842	Remote Similarity	NPD4695	Discontinued
0.6832	Remote Similarity	NPD5692	Phase 3
0.6809	Remote Similarity	NPD5364	Discontinued
0.6786	Remote Similarity	NPD5127	Approved
0.6774	Remote Similarity	NPD6117	Approved
0.6765	Remote Similarity	NPD5284	Approved
0.6765	Remote Similarity	NPD5281	Approved
0.6765	Remote Similarity	NPD5694	Approved
0.6742	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7645	Phase 2
0.6737	Remote Similarity	NPD4195	Approved
0.6727	Remote Similarity	NPD6412	Phase 2
0.6702	Remote Similarity	NPD6116	Phase 1
0.6701	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5133	Approved
0.6698	Remote Similarity	NPD5290	Discontinued
0.6696	Remote Similarity	NPD6868	Approved
0.6696	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD7101	Approved
0.6638	Remote Similarity	NPD6317	Approved
0.6632	Remote Similarity	NPD6697	Approved
0.6632	Remote Similarity	NPD6115	Approved
0.6632	Remote Similarity	NPD6118	Approved
0.6632	Remote Similarity	NPD6114	Approved
0.661	Remote Similarity	NPD6319	Approved
0.661	Remote Similarity	NPD6054	Approved
0.661	Remote Similarity	NPD6059	Approved
0.6609	Remote Similarity	NPD5167	Approved
0.6606	Remote Similarity	NPD6052	Approved
0.6604	Remote Similarity	NPD5959	Approved
0.66	Remote Similarity	NPD4519	Discontinued
0.66	Remote Similarity	NPD4623	Approved
0.6596	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7604	Phase 2
0.6581	Remote Similarity	NPD6335	Approved
0.6569	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5360	Phase 3
0.6556	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6909	Approved
0.6555	Remote Similarity	NPD6908	Approved
0.6514	Remote Similarity	NPD7632	Discontinued
0.6505	Remote Similarity	NPD4096	Approved
0.65	Remote Similarity	NPD1694	Approved
0.65	Remote Similarity	NPD6370	Approved
0.6496	Remote Similarity	NPD6009	Approved
0.6489	Remote Similarity	NPD3703	Phase 2
0.6475	Remote Similarity	NPD7507	Approved
0.6441	Remote Similarity	NPD6314	Approved
0.6441	Remote Similarity	NPD6313	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