NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.16
Volume:	260.554
LogP:	4.074
LogD:	3.961
LogS:	-4.083
# Rotatable Bonds:	0
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.363
Synthetic Accessibility Score:	4.167
Fsp3:	0.667
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:	-4.646
MDCK Permeability:	3.2443196687381715e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.358
20% Bioavailability (F20%):	0.869
30% Bioavailability (F30%):	0.786

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.165
Plasma Protein Binding (PPB):	95.80339813232422%
Volume Distribution (VD):	1.073
Pgp-substrate:	3.2665934562683105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.814
CYP1A2-substrate:	0.594
CYP2C19-inhibitor:	0.774
CYP2C19-substrate:	0.271
CYP2C9-inhibitor:	0.761
CYP2C9-substrate:	0.441
CYP2D6-inhibitor:	0.165
CYP2D6-substrate:	0.287
CYP3A4-inhibitor:	0.267
CYP3A4-substrate:	0.174

ADMET: Excretion

Clearance (CL):	7.702
Half-life (T1/2):	0.189

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.423
Drug-inuced Liver Injury (DILI):	0.533
AMES Toxicity:	0.527
Rat Oral Acute Toxicity:	0.84
Maximum Recommended Daily Dose:	0.301
Skin Sensitization:	0.834
Carcinogencity:	0.216
Eye Corrosion:	0.909
Eye Irritation:	0.661
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: NPC235906

Natural Product ID:	NPC235906
*Common Name:**	Isodihydrocostunolide
IUPAC Name:	(3aR,6S,10E,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,6,7,8,9,11a-octahydrocyclodeca[b]furan-2-one
Synonyms:	Isodihydrocostunolide
Standard InCHIKey:	DCNAVROPXHTJGM-DKWJYAAYSA-N
Standard InCHI:	InChI=1S/C15H22O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h9-10,13-14H,3-8H2,1-2H3/b11-9+/t10-,13+,14+/m0/s1
SMILES:	C[C@H]1CCC/C(=C/[C@@H]2[C@H](CC1)C(=C)C(=O)O2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481693
PubChem CID:	24893995
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides 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
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	root	n.a.	PMID[18409040]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	roots	n.a.	n.a.	PMID[18579374]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25068579]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	root	n.a.	PMID[8541643]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	27.03	ug.mL-1	PMID[525995]
NPT762	Cell Line	A-431	Homo sapiens	IC50	=	107.0	ug.mL-1	PMID[525995]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	35.05	ug.mL-1	PMID[525995]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	125.0	ug.mL-1	PMID[525995]

☑ 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 NPC235906 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	185
0.1-0.2	1265
0.2-0.3	5872
0.3-0.4	15689
0.4-0.5	9987
0.5-0.6	6298
0.6-0.7	2607
0.7-0.8	609
0.8-0.85	106
0.85-0.9	57
0.9-0.95	16
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9577	High Similarity	NPC155587
0.9571	High Similarity	NPC295633
0.9571	High Similarity	NPC269206
0.9571	High Similarity	NPC58956
0.9315	High Similarity	NPC65603
0.9155	High Similarity	NPC163003
0.9155	High Similarity	NPC129665
0.9054	High Similarity	NPC470240
0.9054	High Similarity	NPC187568
0.9054	High Similarity	NPC171204
0.9054	High Similarity	NPC476794
0.9054	High Similarity	NPC141789
0.9054	High Similarity	NPC476028
0.9054	High Similarity	NPC41780
0.9041	High Similarity	NPC226669
0.9041	High Similarity	NPC193351
0.9041	High Similarity	NPC138408
0.8974	High Similarity	NPC114979
0.8974	High Similarity	NPC191476
0.8933	High Similarity	NPC196653
0.8933	High Similarity	NPC471465
0.8904	High Similarity	NPC140287
0.8904	High Similarity	NPC476355
0.8861	High Similarity	NPC255307
0.8831	High Similarity	NPC301477
0.8831	High Similarity	NPC281949
0.8831	High Similarity	NPC141810
0.8831	High Similarity	NPC25684
0.8816	High Similarity	NPC182550
0.8816	High Similarity	NPC470244
0.8816	High Similarity	NPC270126
0.8816	High Similarity	NPC470239
0.8816	High Similarity	NPC167881
0.8816	High Similarity	NPC617
0.8816	High Similarity	NPC98557
0.8816	High Similarity	NPC89128
0.875	High Similarity	NPC305475
0.875	High Similarity	NPC475461
0.875	High Similarity	NPC50637
0.8734	High Similarity	NPC141193
0.8734	High Similarity	NPC96259
0.8718	High Similarity	NPC229825
0.8701	High Similarity	NPC302426
0.8701	High Similarity	NPC281132
0.8701	High Similarity	NPC276356
0.8667	High Similarity	NPC123360
0.8608	High Similarity	NPC474703
0.8608	High Similarity	NPC131669
0.8608	High Similarity	NPC473390
0.859	High Similarity	NPC24417
0.8571	High Similarity	NPC264227
0.8571	High Similarity	NPC472965
0.8571	High Similarity	NPC63649
0.8553	High Similarity	NPC7563
0.8553	High Similarity	NPC97516
0.8553	High Similarity	NPC474760
0.8553	High Similarity	NPC116177
0.8553	High Similarity	NPC320630
0.8519	High Similarity	NPC150755
0.85	High Similarity	NPC476804
0.8481	Intermediate Similarity	NPC173609
0.8481	Intermediate Similarity	NPC178676
0.8462	Intermediate Similarity	NPC69271
0.8462	Intermediate Similarity	NPC74673
0.8442	Intermediate Similarity	NPC108816
0.8442	Intermediate Similarity	NPC267231
0.8442	Intermediate Similarity	NPC472960
0.8442	Intermediate Similarity	NPC128276
0.8442	Intermediate Similarity	NPC93763
0.8434	Intermediate Similarity	NPC166919
0.8395	Intermediate Similarity	NPC165162
0.8395	Intermediate Similarity	NPC50362
0.8395	Intermediate Similarity	NPC38468
0.8395	Intermediate Similarity	NPC319795
0.8375	Intermediate Similarity	NPC215294
0.8375	Intermediate Similarity	NPC169575
0.8375	Intermediate Similarity	NPC318468
0.8375	Intermediate Similarity	NPC272814
0.8375	Intermediate Similarity	NPC40746
0.8375	Intermediate Similarity	NPC39588
0.8375	Intermediate Similarity	NPC59097
0.8375	Intermediate Similarity	NPC250315
0.8354	Intermediate Similarity	NPC35089
0.8354	Intermediate Similarity	NPC52861
0.8354	Intermediate Similarity	NPC471325
0.8354	Intermediate Similarity	NPC10276
0.8333	Intermediate Similarity	NPC194871
0.8333	Intermediate Similarity	NPC178277
0.8333	Intermediate Similarity	NPC469368
0.8312	Intermediate Similarity	NPC57744
0.8293	Intermediate Similarity	NPC107787
0.8293	Intermediate Similarity	NPC284902
0.8272	Intermediate Similarity	NPC115786
0.8272	Intermediate Similarity	NPC158756
0.8272	Intermediate Similarity	NPC159635
0.825	Intermediate Similarity	NPC89555
0.8243	Intermediate Similarity	NPC472955
0.8228	Intermediate Similarity	NPC223904
0.8219	Intermediate Similarity	NPC470256
0.8214	Intermediate Similarity	NPC151770
0.8214	Intermediate Similarity	NPC474032
0.8205	Intermediate Similarity	NPC299235
0.8193	Intermediate Similarity	NPC475703
0.8193	Intermediate Similarity	NPC231889
0.8171	Intermediate Similarity	NPC215364
0.8171	Intermediate Similarity	NPC78089
0.8171	Intermediate Similarity	NPC110405
0.8171	Intermediate Similarity	NPC470755
0.8171	Intermediate Similarity	NPC161957
0.8171	Intermediate Similarity	NPC33570
0.8171	Intermediate Similarity	NPC21471
0.8158	Intermediate Similarity	NPC143979
0.8158	Intermediate Similarity	NPC320537
0.8148	Intermediate Similarity	NPC22611
0.8148	Intermediate Similarity	NPC475947
0.814	Intermediate Similarity	NPC475838
0.814	Intermediate Similarity	NPC475302
0.814	Intermediate Similarity	NPC125674
0.814	Intermediate Similarity	NPC228451
0.8125	Intermediate Similarity	NPC42470
0.8125	Intermediate Similarity	NPC325031
0.8118	Intermediate Similarity	NPC475855
0.8118	Intermediate Similarity	NPC312042
0.8118	Intermediate Similarity	NPC144133
0.8118	Intermediate Similarity	NPC179394
0.8108	Intermediate Similarity	NPC144511
0.8108	Intermediate Similarity	NPC199557
0.8108	Intermediate Similarity	NPC296522
0.8095	Intermediate Similarity	NPC476803
0.8095	Intermediate Similarity	NPC476805
0.8077	Intermediate Similarity	NPC15975
0.8077	Intermediate Similarity	NPC53581
0.8077	Intermediate Similarity	NPC195785
0.8077	Intermediate Similarity	NPC103987
0.8072	Intermediate Similarity	NPC279859
0.8072	Intermediate Similarity	NPC38576
0.8072	Intermediate Similarity	NPC469910
0.8052	Intermediate Similarity	NPC244166
0.8049	Intermediate Similarity	NPC156485
0.8046	Intermediate Similarity	NPC140543
0.8046	Intermediate Similarity	NPC474247
0.8046	Intermediate Similarity	NPC473330
0.8046	Intermediate Similarity	NPC473316
0.8026	Intermediate Similarity	NPC472956
0.8025	Intermediate Similarity	NPC35556
0.8025	Intermediate Similarity	NPC85772
0.8	Intermediate Similarity	NPC295312
0.8	Intermediate Similarity	NPC195424
0.8	Intermediate Similarity	NPC268298
0.7976	Intermediate Similarity	NPC160138
0.7976	Intermediate Similarity	NPC266957
0.7973	Intermediate Similarity	NPC218477
0.7955	Intermediate Similarity	NPC471141
0.7952	Intermediate Similarity	NPC235792
0.7952	Intermediate Similarity	NPC261380
0.7952	Intermediate Similarity	NPC177932
0.7949	Intermediate Similarity	NPC472967
0.7949	Intermediate Similarity	NPC472959
0.7949	Intermediate Similarity	NPC266159
0.7949	Intermediate Similarity	NPC68819
0.7927	Intermediate Similarity	NPC193198
0.7927	Intermediate Similarity	NPC170286
0.7927	Intermediate Similarity	NPC53867
0.7922	Intermediate Similarity	NPC15499
0.7922	Intermediate Similarity	NPC472966
0.7922	Intermediate Similarity	NPC259599
0.7922	Intermediate Similarity	NPC117746
0.7922	Intermediate Similarity	NPC294434
0.7907	Intermediate Similarity	NPC51004
0.7907	Intermediate Similarity	NPC301969
0.7907	Intermediate Similarity	NPC129419
0.7907	Intermediate Similarity	NPC475748
0.7907	Intermediate Similarity	NPC62815
0.7907	Intermediate Similarity	NPC251385
0.7907	Intermediate Similarity	NPC49342
0.7907	Intermediate Similarity	NPC37607
0.7901	Intermediate Similarity	NPC38642
0.7882	Intermediate Similarity	NPC226863
0.7882	Intermediate Similarity	NPC202672
0.7882	Intermediate Similarity	NPC477302
0.7882	Intermediate Similarity	NPC215831
0.7882	Intermediate Similarity	NPC136879
0.7882	Intermediate Similarity	NPC91248
0.7882	Intermediate Similarity	NPC473715
0.7882	Intermediate Similarity	NPC475819
0.7867	Intermediate Similarity	NPC265574
0.7865	Intermediate Similarity	NPC230800
0.7865	Intermediate Similarity	NPC279621
0.7857	Intermediate Similarity	NPC261721
0.7857	Intermediate Similarity	NPC64153
0.7857	Intermediate Similarity	NPC67493
0.7848	Intermediate Similarity	NPC208223
0.7848	Intermediate Similarity	NPC122264
0.7841	Intermediate Similarity	NPC471147
0.7841	Intermediate Similarity	NPC303942
0.7841	Intermediate Similarity	NPC57405
0.7841	Intermediate Similarity	NPC476596
0.7841	Intermediate Similarity	NPC476267
0.7838	Intermediate Similarity	NPC472266
0.7831	Intermediate Similarity	NPC30486

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 NPC235906 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1802
0.2-0.3	3971
0.3-0.4	2184
0.4-0.5	693
0.5-0.6	260
0.6-0.7	53
0.7-0.8	10
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
0.8395	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD1694	Approved
0.7791	Intermediate Similarity	NPD1695	Approved
0.759	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD8039	Approved
0.7111	Intermediate Similarity	NPD5785	Approved
0.7093	Intermediate Similarity	NPD7154	Phase 3
0.6977	Remote Similarity	NPD5209	Approved
0.6932	Remote Similarity	NPD5363	Approved
0.6923	Remote Similarity	NPD6698	Approved
0.6923	Remote Similarity	NPD46	Approved
0.6897	Remote Similarity	NPD5362	Discontinued
0.68	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4269	Approved
0.6782	Remote Similarity	NPD4270	Approved
0.6771	Remote Similarity	NPD4225	Approved
0.6742	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6559	Remote Similarity	NPD7838	Discovery
0.6552	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4252	Approved
0.6522	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6903	Approved
0.6512	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6371	Approved
0.6421	Remote Similarity	NPD6399	Phase 3
0.6421	Remote Similarity	NPD5779	Approved
0.6421	Remote Similarity	NPD5778	Approved
0.6404	Remote Similarity	NPD6435	Approved
0.6364	Remote Similarity	NPD4821	Approved
0.6364	Remote Similarity	NPD4822	Approved
0.6364	Remote Similarity	NPD4820	Approved
0.6364	Remote Similarity	NPD4819	Approved
0.6344	Remote Similarity	NPD6672	Approved
0.6344	Remote Similarity	NPD5737	Approved
0.6333	Remote Similarity	NPD5331	Approved
0.6333	Remote Similarity	NPD5332	Approved
0.6322	Remote Similarity	NPD4271	Approved
0.6322	Remote Similarity	NPD4268	Approved
0.6316	Remote Similarity	NPD7983	Approved
0.6316	Remote Similarity	NPD5693	Phase 1
0.6304	Remote Similarity	NPD4249	Approved
0.6292	Remote Similarity	NPD4790	Discontinued
0.6277	Remote Similarity	NPD6101	Approved
0.6277	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7638	Approved
0.6263	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6686	Approved
0.625	Remote Similarity	NPD6927	Phase 3
0.6237	Remote Similarity	NPD4250	Approved
0.6237	Remote Similarity	NPD4251	Approved
0.6226	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5207	Approved
0.6207	Remote Similarity	NPD4756	Discovery
0.62	Remote Similarity	NPD7640	Approved
0.62	Remote Similarity	NPD7639	Approved
0.6186	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5282	Discontinued
0.6186	Remote Similarity	NPD7900	Approved
0.618	Remote Similarity	NPD5368	Approved
0.6146	Remote Similarity	NPD6411	Approved
0.6129	Remote Similarity	NPD6422	Discontinued
0.6125	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5370	Suspended
0.6105	Remote Similarity	NPD6051	Approved
0.6091	Remote Similarity	NPD7115	Discovery
0.6087	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD3573	Approved
0.6061	Remote Similarity	NPD7839	Suspended
0.6061	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6008	Approved
0.6044	Remote Similarity	NPD3667	Approved
0.6027	Remote Similarity	NPD29	Approved
0.6027	Remote Similarity	NPD28	Approved
0.602	Remote Similarity	NPD6001	Approved
0.602	Remote Similarity	NPD7748	Approved
0.6019	Remote Similarity	NPD6053	Discontinued
0.6	Remote Similarity	NPD5208	Approved
0.6	Remote Similarity	NPD7902	Approved
0.5981	Remote Similarity	NPD2067	Discontinued
0.5979	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD7331	Phase 2
0.5976	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5695	Phase 3
0.5957	Remote Similarity	NPD6098	Approved
0.5957	Remote Similarity	NPD3618	Phase 1
0.5941	Remote Similarity	NPD5696	Approved
0.5938	Remote Similarity	NPD6080	Approved
0.5938	Remote Similarity	NPD6904	Approved
0.5938	Remote Similarity	NPD6673	Approved
0.5926	Remote Similarity	NPD3197	Phase 1
0.5914	Remote Similarity	NPD3665	Phase 1
0.5914	Remote Similarity	NPD4786	Approved
0.5914	Remote Similarity	NPD3666	Approved
0.5914	Remote Similarity	NPD3668	Phase 3
0.5914	Remote Similarity	NPD3133	Approved
0.5882	Remote Similarity	NPD6648	Approved
0.5876	Remote Similarity	NPD5692	Phase 3
0.5867	Remote Similarity	NPD3172	Approved
0.5854	Remote Similarity	NPD7341	Phase 2
0.5849	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD6084	Phase 2
0.5842	Remote Similarity	NPD6083	Phase 2
0.5825	Remote Similarity	NPD5344	Discontinued
0.5824	Remote Similarity	NPD4695	Discontinued
0.5816	Remote Similarity	NPD6050	Approved
0.5816	Remote Similarity	NPD7515	Phase 2
0.5816	Remote Similarity	NPD5694	Approved
0.5816	Remote Similarity	NPD7637	Suspended
0.5789	Remote Similarity	NPD3195	Phase 2
0.5789	Remote Similarity	NPD4266	Approved
0.5789	Remote Similarity	NPD9298	Approved
0.5789	Remote Similarity	NPD5279	Phase 3
0.5789	Remote Similarity	NPD3196	Approved
0.5789	Remote Similarity	NPD3194	Approved
0.5761	Remote Similarity	NPD857	Phase 3
0.575	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.575	Remote Similarity	NPD1145	Discontinued
0.5701	Remote Similarity	NPD5697	Approved
0.5688	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD8034	Phase 2
0.5657	Remote Similarity	NPD5281	Approved
0.5657	Remote Similarity	NPD8035	Phase 2
0.5657	Remote Similarity	NPD6079	Approved
0.5657	Remote Similarity	NPD5284	Approved
0.5648	Remote Similarity	NPD6899	Approved
0.5648	Remote Similarity	NPD6011	Approved
0.5648	Remote Similarity	NPD6881	Approved
0.5636	Remote Similarity	NPD6650	Approved
0.5636	Remote Similarity	NPD6649	Approved
0.5625	Remote Similarity	NPD4519	Discontinued
0.5625	Remote Similarity	NPD4623	Approved
0.5619	Remote Similarity	NPD7632	Discontinued
0.5616	Remote Similarity	NPD5343	Approved
0.5612	Remote Similarity	NPD5328	Approved
0.561	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD5739	Approved
0.5607	Remote Similarity	NPD6675	Approved
0.5607	Remote Similarity	NPD6402	Approved
0.5607	Remote Similarity	NPD7128	Approved
0.5603	Remote Similarity	NPD8517	Approved
0.5603	Remote Similarity	NPD8513	Phase 3
0.5603	Remote Similarity	NPD8515	Approved
0.5603	Remote Similarity	NPD8516	Approved
0.56	Remote Similarity	NPD5781	Clinical (unspecified phase)

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