NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	448.21
Volume:	446.574
LogP:	2.472
LogD:	2.638
LogS:	-4.083
# Rotatable Bonds:	7
TPSA:	105.2
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.208
Synthetic Accessibility Score:	5.073
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.259
MDCK Permeability:	4.525289114098996e-05
Pgp-inhibitor:	0.949
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.783
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.983
Plasma Protein Binding (PPB):	66.58704376220703%
Volume Distribution (VD):	1.384
Pgp-substrate:	43.92815017700195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.943
CYP2C19-inhibitor:	0.196
CYP2C19-substrate:	0.731
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.941
CYP3A4-substrate:	0.829

ADMET: Excretion

Clearance (CL):	11.128
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.7
Drug-inuced Liver Injury (DILI):	0.297
AMES Toxicity:	0.928
Rat Oral Acute Toxicity:	0.525
Maximum Recommended Daily Dose:	0.477
Skin Sensitization:	0.324
Carcinogencity:	0.329
Eye Corrosion:	0.364
Eye Irritation:	0.271
Respiratory Toxicity:	0.621

Download Data

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

Natural Product: NPC476770

Natural Product ID:	NPC476770
*Common Name:**	dimethyl (6aS,7R,10aR,11aS,11bS)-10a-ethoxy-11b-formyl-7-methyl-9-oxo-1,2,3,4a,5,6,6a,7,11,11a-decahydronaphtho[2,1-f][1]benzofuran-4,4-dicarboxylate
IUPAC Name:	dimethyl (6aS,7R,10aR,11aS,11bS)-10a-ethoxy-11b-formyl-7-methyl-9-oxo-1,2,3,4a,5,6,6a,7,11,11a-decahydronaphtho[2,1-f][1]benzofuran-4,4-dicarboxylate
Synonyms:
Standard InCHIKey:	XOBQCHDBHSHTED-XJZWDQOVSA-N
Standard InCHI:	InChI=1S/C24H32O8/c1-5-31-24-12-17-15(14(2)16(24)11-19(26)32-24)7-8-18-22(17,13-25)9-6-10-23(18,20(27)29-3)21(28)30-4/h11,13-15,17-18H,5-10,12H2,1-4H3/t14-,15+,17+,18?,22+,24-/m1/s1
SMILES:	CCO[C@@]12C[C@H]3[C@@H](CCC4[C@@]3(CCCC4(C(=O)OC)C(=O)OC)C=O)[C@H](C1=CC(=O)O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122195861
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids [CHEMONTID:0003557] 19-oxosteroids

*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
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[19420770]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23127886]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23234407]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	seeds	Nanning, Guangxi Province, China	2013-APR	PMID[26398312]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	38900	nM	PMID[26398312]

☑ 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 NPC476770 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	256
0.1-0.2	1552
0.2-0.3	4972
0.3-0.4	9593
0.4-0.5	12991
0.5-0.6	7270
0.6-0.7	5180
0.7-0.8	860
0.8-0.85	14
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC476768
0.8824	High Similarity	NPC476762
0.8824	High Similarity	NPC476760
0.8824	High Similarity	NPC476761
0.8725	High Similarity	NPC476764
0.8725	High Similarity	NPC476763
0.8713	High Similarity	NPC476769
0.8396	Intermediate Similarity	NPC476759
0.8384	Intermediate Similarity	NPC84893
0.8333	Intermediate Similarity	NPC117685
0.8318	Intermediate Similarity	NPC476766
0.8283	Intermediate Similarity	NPC472303
0.8265	Intermediate Similarity	NPC8062
0.8182	Intermediate Similarity	NPC289479
0.8155	Intermediate Similarity	NPC476767
0.8131	Intermediate Similarity	NPC476765
0.8039	Intermediate Similarity	NPC325960
0.8039	Intermediate Similarity	NPC319692
0.7981	Intermediate Similarity	NPC475202
0.7981	Intermediate Similarity	NPC475392
0.7981	Intermediate Similarity	NPC475385
0.7946	Intermediate Similarity	NPC469794
0.7946	Intermediate Similarity	NPC72772
0.7938	Intermediate Similarity	NPC474013
0.7925	Intermediate Similarity	NPC471364
0.7925	Intermediate Similarity	NPC132395
0.7925	Intermediate Similarity	NPC471365
0.79	Intermediate Similarity	NPC161638
0.79	Intermediate Similarity	NPC328141
0.79	Intermediate Similarity	NPC101651
0.79	Intermediate Similarity	NPC159748
0.789	Intermediate Similarity	NPC112457
0.787	Intermediate Similarity	NPC475570
0.7864	Intermediate Similarity	NPC242848
0.7843	Intermediate Similarity	NPC269729
0.7822	Intermediate Similarity	NPC329842
0.7818	Intermediate Similarity	NPC472666
0.7812	Intermediate Similarity	NPC200513
0.781	Intermediate Similarity	NPC476299
0.781	Intermediate Similarity	NPC474012
0.781	Intermediate Similarity	NPC471413
0.78	Intermediate Similarity	NPC174342
0.7798	Intermediate Similarity	NPC473483
0.7788	Intermediate Similarity	NPC204054
0.7788	Intermediate Similarity	NPC475709
0.7788	Intermediate Similarity	NPC38530
0.7788	Intermediate Similarity	NPC257726
0.7788	Intermediate Similarity	NPC2049
0.7788	Intermediate Similarity	NPC84335
0.7767	Intermediate Similarity	NPC274417
0.7757	Intermediate Similarity	NPC254202
0.7757	Intermediate Similarity	NPC120321
0.7757	Intermediate Similarity	NPC112009
0.7757	Intermediate Similarity	NPC180204
0.7755	Intermediate Similarity	NPC189311
0.775	Intermediate Similarity	NPC471361
0.775	Intermediate Similarity	NPC6108
0.775	Intermediate Similarity	NPC284406
0.775	Intermediate Similarity	NPC469754
0.775	Intermediate Similarity	NPC471360
0.775	Intermediate Similarity	NPC471359
0.775	Intermediate Similarity	NPC9499
0.775	Intermediate Similarity	NPC17896
0.775	Intermediate Similarity	NPC469751
0.775	Intermediate Similarity	NPC70542
0.775	Intermediate Similarity	NPC469753
0.775	Intermediate Similarity	NPC471352
0.775	Intermediate Similarity	NPC219085
0.775	Intermediate Similarity	NPC10823
0.775	Intermediate Similarity	NPC471358
0.775	Intermediate Similarity	NPC469752
0.775	Intermediate Similarity	NPC86159
0.775	Intermediate Similarity	NPC180079
0.775	Intermediate Similarity	NPC197707
0.775	Intermediate Similarity	NPC251866
0.775	Intermediate Similarity	NPC89514
0.775	Intermediate Similarity	NPC469755
0.7745	Intermediate Similarity	NPC139692
0.7745	Intermediate Similarity	NPC474185
0.7736	Intermediate Similarity	NPC471412
0.7736	Intermediate Similarity	NPC471075
0.7736	Intermediate Similarity	NPC476888
0.7736	Intermediate Similarity	NPC310981
0.7736	Intermediate Similarity	NPC93744
0.7723	Intermediate Similarity	NPC51486
0.7719	Intermediate Similarity	NPC474483
0.77	Intermediate Similarity	NPC80335
0.77	Intermediate Similarity	NPC472302
0.7692	Intermediate Similarity	NPC164750
0.7692	Intermediate Similarity	NPC106425
0.7692	Intermediate Similarity	NPC471039
0.7692	Intermediate Similarity	NPC122324
0.7692	Intermediate Similarity	NPC29952
0.7692	Intermediate Similarity	NPC151725
0.7685	Intermediate Similarity	NPC470297
0.7685	Intermediate Similarity	NPC189616
0.7677	Intermediate Similarity	NPC220478
0.767	Intermediate Similarity	NPC471040
0.767	Intermediate Similarity	NPC470697
0.767	Intermediate Similarity	NPC477722
0.7664	Intermediate Similarity	NPC162973
0.7664	Intermediate Similarity	NPC40918
0.7664	Intermediate Similarity	NPC476890
0.7653	Intermediate Similarity	NPC149869
0.7653	Intermediate Similarity	NPC71626
0.7647	Intermediate Similarity	NPC472814
0.7647	Intermediate Similarity	NPC250556
0.7647	Intermediate Similarity	NPC177037
0.7647	Intermediate Similarity	NPC469750
0.7642	Intermediate Similarity	NPC201406
0.7642	Intermediate Similarity	NPC477720
0.7636	Intermediate Similarity	NPC90946
0.7636	Intermediate Similarity	NPC300614
0.7624	Intermediate Similarity	NPC50070
0.7624	Intermediate Similarity	NPC469546
0.7619	Intermediate Similarity	NPC110937
0.7615	Intermediate Similarity	NPC1679
0.7611	Intermediate Similarity	NPC157441
0.7593	Intermediate Similarity	NPC476889
0.7593	Intermediate Similarity	NPC291154
0.7593	Intermediate Similarity	NPC473283
0.7593	Intermediate Similarity	NPC329345
0.7593	Intermediate Similarity	NPC475526
0.7583	Intermediate Similarity	NPC469757
0.7583	Intermediate Similarity	NPC471357
0.7583	Intermediate Similarity	NPC146456
0.7583	Intermediate Similarity	NPC117702
0.7583	Intermediate Similarity	NPC471356
0.7583	Intermediate Similarity	NPC179412
0.7576	Intermediate Similarity	NPC472442
0.7576	Intermediate Similarity	NPC65661
0.7573	Intermediate Similarity	NPC115021
0.757	Intermediate Similarity	NPC303559
0.757	Intermediate Similarity	NPC472643
0.757	Intermediate Similarity	NPC474899
0.757	Intermediate Similarity	NPC474912
0.7568	Intermediate Similarity	NPC474243
0.7568	Intermediate Similarity	NPC31522
0.7561	Intermediate Similarity	NPC146857
0.7561	Intermediate Similarity	NPC116075
0.7561	Intermediate Similarity	NPC247190
0.7561	Intermediate Similarity	NPC88668
0.7561	Intermediate Similarity	NPC469749
0.7561	Intermediate Similarity	NPC32793
0.7551	Intermediate Similarity	NPC472440
0.7549	Intermediate Similarity	NPC477782
0.7547	Intermediate Similarity	NPC469986
0.7547	Intermediate Similarity	NPC176845
0.7545	Intermediate Similarity	NPC179380
0.7526	Intermediate Similarity	NPC282293
0.7525	Intermediate Similarity	NPC93411
0.7525	Intermediate Similarity	NPC226863
0.7524	Intermediate Similarity	NPC134072
0.7524	Intermediate Similarity	NPC17578
0.7524	Intermediate Similarity	NPC112654
0.7524	Intermediate Similarity	NPC234993
0.7524	Intermediate Similarity	NPC240673
0.7523	Intermediate Similarity	NPC474898
0.7522	Intermediate Similarity	NPC194951
0.7522	Intermediate Similarity	NPC277769
0.7522	Intermediate Similarity	NPC12046
0.7522	Intermediate Similarity	NPC4573
0.7522	Intermediate Similarity	NPC285956
0.7522	Intermediate Similarity	NPC90952
0.7521	Intermediate Similarity	NPC476150
0.7521	Intermediate Similarity	NPC476127
0.75	Intermediate Similarity	NPC476081
0.75	Intermediate Similarity	NPC471078
0.75	Intermediate Similarity	NPC148463
0.75	Intermediate Similarity	NPC470496
0.75	Intermediate Similarity	NPC473431
0.75	Intermediate Similarity	NPC473280
0.75	Intermediate Similarity	NPC329636
0.75	Intermediate Similarity	NPC134077
0.75	Intermediate Similarity	NPC473435
0.7479	Intermediate Similarity	NPC27363
0.7479	Intermediate Similarity	NPC55602
0.7478	Intermediate Similarity	NPC471816
0.7478	Intermediate Similarity	NPC196931
0.7477	Intermediate Similarity	NPC35751
0.7477	Intermediate Similarity	NPC472644
0.7477	Intermediate Similarity	NPC189075
0.7477	Intermediate Similarity	NPC89171
0.7477	Intermediate Similarity	NPC392
0.7477	Intermediate Similarity	NPC476933
0.7477	Intermediate Similarity	NPC476802
0.7477	Intermediate Similarity	NPC470761
0.7477	Intermediate Similarity	NPC471041
0.7477	Intermediate Similarity	NPC177524
0.7477	Intermediate Similarity	NPC306265
0.7477	Intermediate Similarity	NPC61411
0.7477	Intermediate Similarity	NPC473219
0.7477	Intermediate Similarity	NPC470906
0.7477	Intermediate Similarity	NPC219900
0.7477	Intermediate Similarity	NPC275539
0.7476	Intermediate Similarity	NPC477783
0.7476	Intermediate Similarity	NPC65513
0.7476	Intermediate Similarity	NPC141831
0.7475	Intermediate Similarity	NPC318515
0.7475	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 NPC476770 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	1750
0.2-0.3	3914
0.3-0.4	2129
0.4-0.5	740
0.5-0.6	211
0.6-0.7	163
0.7-0.8	11
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
0.7812	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7319	Approved
0.7647	Intermediate Similarity	NPD7507	Approved
0.7477	Intermediate Similarity	NPD6686	Approved
0.7383	Intermediate Similarity	NPD7638	Approved
0.7315	Intermediate Similarity	NPD7640	Approved
0.7315	Intermediate Similarity	NPD7639	Approved
0.7217	Intermediate Similarity	NPD6882	Approved
0.7184	Intermediate Similarity	NPD5737	Approved
0.7184	Intermediate Similarity	NPD6672	Approved
0.7184	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7748	Approved
0.717	Intermediate Similarity	NPD7900	Approved
0.7157	Intermediate Similarity	NPD7146	Approved
0.7157	Intermediate Similarity	NPD7521	Approved
0.7157	Intermediate Similarity	NPD7334	Approved
0.7157	Intermediate Similarity	NPD6684	Approved
0.7157	Intermediate Similarity	NPD6409	Approved
0.7157	Intermediate Similarity	NPD5330	Approved
0.7087	Intermediate Similarity	NPD3573	Approved
0.7064	Intermediate Similarity	NPD4225	Approved
0.7019	Intermediate Similarity	NPD6903	Approved
0.6991	Remote Similarity	NPD7128	Approved
0.6991	Remote Similarity	NPD6675	Approved
0.6991	Remote Similarity	NPD5739	Approved
0.6991	Remote Similarity	NPD6402	Approved
0.6981	Remote Similarity	NPD7515	Phase 2
0.6981	Remote Similarity	NPD5693	Phase 1
0.6975	Remote Similarity	NPD7115	Discovery
0.6972	Remote Similarity	NPD7902	Approved
0.6957	Remote Similarity	NPD6372	Approved
0.6957	Remote Similarity	NPD6373	Approved
0.693	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD8328	Phase 3
0.6893	Remote Similarity	NPD1694	Approved
0.687	Remote Similarity	NPD6899	Approved
0.687	Remote Similarity	NPD6881	Approved
0.687	Remote Similarity	NPD7320	Approved
0.6838	Remote Similarity	NPD6650	Approved
0.6838	Remote Similarity	NPD6649	Approved
0.6822	Remote Similarity	NPD6411	Approved
0.6818	Remote Similarity	NPD6084	Phase 2
0.6818	Remote Similarity	NPD6083	Phase 2
0.6792	Remote Similarity	NPD6080	Approved
0.6792	Remote Similarity	NPD5328	Approved
0.6792	Remote Similarity	NPD6904	Approved
0.6792	Remote Similarity	NPD6673	Approved
0.6789	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5701	Approved
0.6783	Remote Similarity	NPD5697	Approved
0.678	Remote Similarity	NPD8297	Approved
0.6777	Remote Similarity	NPD7328	Approved
0.6777	Remote Similarity	NPD7327	Approved
0.6759	Remote Similarity	NPD6399	Phase 3
0.6757	Remote Similarity	NPD5696	Approved
0.6752	Remote Similarity	NPD7290	Approved
0.6752	Remote Similarity	NPD6883	Approved
0.6752	Remote Similarity	NPD7102	Approved
0.6752	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4697	Phase 3
0.6726	Remote Similarity	NPD7632	Discontinued
0.6721	Remote Similarity	NPD7516	Approved
0.672	Remote Similarity	NPD7492	Approved
0.6696	Remote Similarity	NPD6008	Approved
0.6695	Remote Similarity	NPD6847	Approved
0.6695	Remote Similarity	NPD6617	Approved
0.6695	Remote Similarity	NPD6869	Approved
0.6695	Remote Similarity	NPD8130	Phase 1
0.6693	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6079	Approved
0.6636	Remote Similarity	NPD6051	Approved
0.6636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6101	Approved
0.6636	Remote Similarity	NPD5695	Phase 3
0.6614	Remote Similarity	NPD7078	Approved
0.6614	Remote Similarity	NPD8293	Discontinued
0.6613	Remote Similarity	NPD8033	Approved
0.6613	Remote Similarity	NPD8378	Approved
0.6613	Remote Similarity	NPD8380	Approved
0.6613	Remote Similarity	NPD8296	Approved
0.6613	Remote Similarity	NPD8335	Approved
0.6613	Remote Similarity	NPD8379	Approved
0.6606	Remote Similarity	NPD5778	Approved
0.6606	Remote Similarity	NPD5779	Approved
0.6583	Remote Similarity	NPD8133	Approved
0.6581	Remote Similarity	NPD6011	Approved
0.6577	Remote Similarity	NPD7732	Phase 3
0.656	Remote Similarity	NPD6370	Approved
0.6557	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5208	Approved
0.6532	Remote Similarity	NPD6319	Approved
0.6518	Remote Similarity	NPD4755	Approved
0.6514	Remote Similarity	NPD6050	Approved
0.6514	Remote Similarity	NPD8035	Phase 2
0.6514	Remote Similarity	NPD8034	Phase 2
0.6509	Remote Similarity	NPD3618	Phase 1
0.6509	Remote Similarity	NPD6098	Approved
0.6496	Remote Similarity	NPD6412	Phase 2
0.6486	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6015	Approved
0.648	Remote Similarity	NPD6016	Approved
0.6441	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD5211	Phase 2
0.6429	Remote Similarity	NPD5988	Approved
0.6429	Remote Similarity	NPD5222	Approved
0.6429	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5221	Approved
0.6423	Remote Similarity	NPD6009	Approved
0.6422	Remote Similarity	NPD5692	Phase 3
0.6415	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4696	Approved
0.6404	Remote Similarity	NPD5286	Approved
0.6404	Remote Similarity	NPD4700	Approved
0.6404	Remote Similarity	NPD5285	Approved
0.64	Remote Similarity	NPD8039	Approved
0.6396	Remote Similarity	NPD6001	Approved
0.6372	Remote Similarity	NPD5173	Approved
0.6364	Remote Similarity	NPD5694	Approved
0.6364	Remote Similarity	NPD6053	Discontinued
0.6355	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD8513	Phase 3
0.6349	Remote Similarity	NPD8515	Approved
0.6349	Remote Similarity	NPD8516	Approved
0.6349	Remote Similarity	NPD8517	Approved
0.6341	Remote Similarity	NPD6274	Approved
0.6341	Remote Similarity	NPD6868	Approved
0.633	Remote Similarity	NPD4753	Phase 2
0.633	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD5141	Approved
0.6321	Remote Similarity	NPD3665	Phase 1
0.6321	Remote Similarity	NPD3668	Phase 3
0.6321	Remote Similarity	NPD3133	Approved
0.6321	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD3666	Approved
0.6321	Remote Similarity	NPD4786	Approved
0.632	Remote Similarity	NPD7100	Approved
0.632	Remote Similarity	NPD7101	Approved
0.6293	Remote Similarity	NPD5224	Approved
0.6293	Remote Similarity	NPD5225	Approved
0.6293	Remote Similarity	NPD5226	Approved
0.6293	Remote Similarity	NPD4633	Approved
0.6286	Remote Similarity	NPD3667	Approved
0.6286	Remote Similarity	NPD5209	Approved
0.6283	Remote Similarity	NPD7614	Phase 1
0.6273	Remote Similarity	NPD5785	Approved
0.6273	Remote Similarity	NPD5207	Approved
0.6271	Remote Similarity	NPD4767	Approved
0.6271	Remote Similarity	NPD4768	Approved
0.625	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.624	Remote Similarity	NPD6335	Approved
0.6239	Remote Similarity	NPD5175	Approved
0.6239	Remote Similarity	NPD5174	Approved
0.622	Remote Similarity	NPD6908	Approved
0.622	Remote Similarity	NPD6909	Approved
0.622	Remote Similarity	NPD7503	Approved
0.6216	Remote Similarity	NPD7637	Suspended
0.6207	Remote Similarity	NPD5223	Approved
0.6204	Remote Similarity	NPD4519	Discontinued
0.6204	Remote Similarity	NPD4623	Approved
0.6198	Remote Similarity	NPD4634	Approved
0.6195	Remote Similarity	NPD5210	Approved
0.6195	Remote Similarity	NPD4629	Approved
0.6183	Remote Similarity	NPD6033	Approved
0.6179	Remote Similarity	NPD4632	Approved
0.6167	Remote Similarity	NPD4729	Approved
0.6167	Remote Similarity	NPD4730	Approved
0.6161	Remote Similarity	NPD4202	Approved
0.616	Remote Similarity	NPD6317	Approved
0.614	Remote Similarity	NPD7839	Suspended
0.6132	Remote Similarity	NPD4223	Phase 3
0.6132	Remote Similarity	NPD4221	Approved
0.6126	Remote Similarity	NPD46	Approved
0.6126	Remote Similarity	NPD6698	Approved
0.6111	Remote Similarity	NPD6314	Approved
0.6111	Remote Similarity	NPD5329	Approved
0.6111	Remote Similarity	NPD6313	Approved
0.6107	Remote Similarity	NPD8074	Phase 3
0.6102	Remote Similarity	NPD4754	Approved
0.6102	Remote Similarity	NPD6052	Approved
0.6095	Remote Similarity	NPD4695	Discontinued
0.609	Remote Similarity	NPD6914	Discontinued
0.6083	Remote Similarity	NPD6614	Approved
0.6071	Remote Similarity	NPD5284	Approved
0.6071	Remote Similarity	NPD5281	Approved
0.6066	Remote Similarity	NPD5247	Approved
0.6066	Remote Similarity	NPD5248	Approved
0.6066	Remote Similarity	NPD5251	Approved
0.6066	Remote Similarity	NPD5250	Approved
0.6066	Remote Similarity	NPD5249	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