NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	658.28
Volume:	670.73
LogP:	5.385
LogD:	4.27
LogS:	-4.077
# Rotatable Bonds:	10
TPSA:	134.8
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.175
Synthetic Accessibility Score:	5.54
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
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:	-5.255
MDCK Permeability:	3.355861554155126e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.057
20% Bioavailability (F20%):	0.976
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.07
Plasma Protein Binding (PPB):	97.14378356933594%
Volume Distribution (VD):	2.559
Pgp-substrate:	7.727118015289307%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.052
CYP2C19-inhibitor:	0.274
CYP2C19-substrate:	0.166
CYP2C9-inhibitor:	0.903
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.936
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.948
CYP3A4-substrate:	0.693

ADMET: Excretion

Clearance (CL):	8.491
Half-life (T1/2):	0.145

ADMET: Toxicity

hERG Blockers:	0.449
Human Hepatotoxicity (H-HT):	0.884
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.901
Maximum Recommended Daily Dose:	0.12
Skin Sensitization:	0.233
Carcinogencity:	0.081
Eye Corrosion:	0.004
Eye Irritation:	0.026
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC477095

Natural Product ID:	NPC477095
*Common Name:**	(1aR,2S,3R,4aR,6S,7S,7aS,8E,10R,11S,11aS)-1,1,3,6,9-Pentamethyl-2,11-diacetoxy-4a,7a-epoxy-7,10-bis(benzoyloxy)-1a,2,3,4,4a,5,6,7,7a,10,11,11a-dodecahydro-1H-cyclopenta[a]cyclopropa[f]cycloundecene-4-one
IUPAC Name:	[(1R,3R,4S,5R,7S,8S,9R,10E,12S,13S,14S)-4,8-diacetyloxy-13-benzoyloxy-3,6,6,10,14-pentamethyl-2-oxo-16-oxatetracyclo[10.3.1.01,12.05,7]hexadec-10-en-9-yl] benzoate
Synonyms:
Standard InCHIKey:	JNOVCEAOWZMYOJ-RZYMXWEKSA-N
Standard InCHI:	InChI=1S/C38H42O10/c1-20-18-38-33(47-35(43)26-16-12-9-13-17-26)21(2)19-37(38,48-38)32(41)22(3)30(44-23(4)39)27-28(36(27,6)7)31(45-24(5)40)29(20)46-34(42)25-14-10-8-11-15-25/h8-18,21-22,27-31,33H,19H2,1-7H3/b20-18+/t21-,22+,27-,28+,29+,30+,31-,33-,37-,38-/m0/s1
SMILES:	C[C@H]1C[C@]23C(=O)[C@@H]([C@H]([C@@H]4[C@@H](C4(C)C)[C@@H]([C@@H](/C(=C/[C@@]2([C@H]1OC(=O)C5=CC=CC=C5)O3)/C)OC(=O)C6=CC=CC=C6)OC(=O)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44179496
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	aerial parts	Yuanjiang, Yunnan Province, China	2008-APR	PMID[19438253]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[30730729]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	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	1
Others	3

Activity Type	# Activity
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	5	ug/ml	PMID[19438253]
NPT2	Others	Unspecified		Inhibition	=	1.8	%	PMID[19438253]

☑ 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 NPC477095 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	393
0.1-0.2	1320
0.2-0.3	2690
0.3-0.4	7130
0.4-0.5	12600
0.5-0.6	12491
0.6-0.7	5318
0.7-0.8	584
0.8-0.85	70
0.85-0.9	59
0.9-0.95	34
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9781	High Similarity	NPC477096
0.9781	High Similarity	NPC477094
0.9781	High Similarity	NPC82467
0.9635	High Similarity	NPC473654
0.958	High Similarity	NPC477098
0.958	High Similarity	NPC477100
0.9562	High Similarity	NPC475660
0.9507	High Similarity	NPC232583
0.9507	High Similarity	NPC25484
0.9489	High Similarity	NPC325805
0.9489	High Similarity	NPC276652
0.9489	High Similarity	NPC272523
0.9416	High Similarity	NPC86772
0.9371	High Similarity	NPC477099
0.9371	High Similarity	NPC477101
0.9371	High Similarity	NPC477097
0.9366	High Similarity	NPC205389
0.9343	High Similarity	NPC285221
0.9343	High Similarity	NPC477358
0.9343	High Similarity	NPC194769
0.927	High Similarity	NPC475262
0.927	High Similarity	NPC270364
0.927	High Similarity	NPC79699
0.927	High Similarity	NPC290833
0.927	High Similarity	NPC265459
0.922	High Similarity	NPC45307
0.9214	High Similarity	NPC473497
0.9197	High Similarity	NPC153617
0.9197	High Similarity	NPC472250
0.9078	High Similarity	NPC474303
0.9078	High Similarity	NPC475413
0.9051	High Similarity	NPC477360
0.8944	High Similarity	NPC242355
0.8944	High Similarity	NPC187566
0.8905	High Similarity	NPC475452
0.8905	High Similarity	NPC475671
0.8905	High Similarity	NPC42234
0.8905	High Similarity	NPC122504
0.8905	High Similarity	NPC3450
0.8897	High Similarity	NPC170668
0.8873	High Similarity	NPC251294
0.8786	High Similarity	NPC477359
0.8716	High Similarity	NPC125033
0.869	High Similarity	NPC153214
0.8671	High Similarity	NPC53361
0.8671	High Similarity	NPC473301
0.8671	High Similarity	NPC121268
0.8652	High Similarity	NPC477368
0.8633	High Similarity	NPC475508
0.8601	High Similarity	NPC327511
0.8601	High Similarity	NPC205305
0.8592	High Similarity	NPC472247
0.8592	High Similarity	NPC279637
0.8592	High Similarity	NPC477367
0.8592	High Similarity	NPC232888
0.8592	High Similarity	NPC149401
0.8582	High Similarity	NPC477364
0.8521	High Similarity	NPC324898
0.8521	High Similarity	NPC298547
0.8521	High Similarity	NPC134937
0.8516	High Similarity	NPC55744
0.8511	High Similarity	NPC233860
0.85	High Similarity	NPC272946
0.8493	Intermediate Similarity	NPC475135
0.8467	Intermediate Similarity	NPC8990
0.8451	Intermediate Similarity	NPC472248
0.8446	Intermediate Similarity	NPC134131
0.8446	Intermediate Similarity	NPC25043
0.8435	Intermediate Similarity	NPC191387
0.8435	Intermediate Similarity	NPC131966
0.8406	Intermediate Similarity	NPC477369
0.8403	Intermediate Similarity	NPC202729
0.8392	Intermediate Similarity	NPC28836
0.8392	Intermediate Similarity	NPC311492
0.838	Intermediate Similarity	NPC239358
0.8345	Intermediate Similarity	NPC27721
0.8344	Intermediate Similarity	NPC254558
0.8333	Intermediate Similarity	NPC200154
0.8322	Intermediate Similarity	NPC471107
0.8322	Intermediate Similarity	NPC471100
0.8312	Intermediate Similarity	NPC70344
0.8298	Intermediate Similarity	NPC37968
0.8286	Intermediate Similarity	NPC477357
0.8252	Intermediate Similarity	NPC233692
0.8194	Intermediate Similarity	NPC11410
0.817	Intermediate Similarity	NPC51602
0.8146	Intermediate Similarity	NPC475552
0.8129	Intermediate Similarity	NPC251139
0.8129	Intermediate Similarity	NPC282239
0.8117	Intermediate Similarity	NPC469648
0.8117	Intermediate Similarity	NPC22571
0.8117	Intermediate Similarity	NPC283875
0.8117	Intermediate Similarity	NPC469647
0.8117	Intermediate Similarity	NPC138641
0.8099	Intermediate Similarity	NPC477370
0.8095	Intermediate Similarity	NPC184109
0.8085	Intermediate Similarity	NPC477363
0.8085	Intermediate Similarity	NPC477366
0.8079	Intermediate Similarity	NPC127857
0.8079	Intermediate Similarity	NPC471162
0.8077	Intermediate Similarity	NPC106895
0.8077	Intermediate Similarity	NPC217091
0.8071	Intermediate Similarity	NPC477362
0.8067	Intermediate Similarity	NPC95449
0.8052	Intermediate Similarity	NPC471103
0.8039	Intermediate Similarity	NPC473403
0.8028	Intermediate Similarity	NPC477365
0.8025	Intermediate Similarity	NPC472393
0.8025	Intermediate Similarity	NPC40138
0.8014	Intermediate Similarity	NPC471911
0.8014	Intermediate Similarity	NPC4242
0.8013	Intermediate Similarity	NPC21410
0.8013	Intermediate Similarity	NPC469456
0.8013	Intermediate Similarity	NPC473670
0.8013	Intermediate Similarity	NPC470231
0.8	Intermediate Similarity	NPC233581
0.8	Intermediate Similarity	NPC145649
0.8	Intermediate Similarity	NPC183540
0.7987	Intermediate Similarity	NPC112216
0.7987	Intermediate Similarity	NPC7095
0.7975	Intermediate Similarity	NPC471102
0.7949	Intermediate Similarity	NPC158333
0.7949	Intermediate Similarity	NPC256142
0.7949	Intermediate Similarity	NPC1173
0.7949	Intermediate Similarity	NPC473414
0.7949	Intermediate Similarity	NPC472030
0.7949	Intermediate Similarity	NPC237549
0.7949	Intermediate Similarity	NPC77719
0.7949	Intermediate Similarity	NPC257213
0.7949	Intermediate Similarity	NPC472022
0.7949	Intermediate Similarity	NPC265395
0.7949	Intermediate Similarity	NPC304876
0.7949	Intermediate Similarity	NPC242262
0.7949	Intermediate Similarity	NPC472005
0.7949	Intermediate Similarity	NPC249471
0.7935	Intermediate Similarity	NPC472398
0.7935	Intermediate Similarity	NPC306799
0.7935	Intermediate Similarity	NPC101043
0.7933	Intermediate Similarity	NPC266374
0.7922	Intermediate Similarity	NPC60509
0.7922	Intermediate Similarity	NPC81698
0.7922	Intermediate Similarity	NPC250046
0.7905	Intermediate Similarity	NPC52523
0.7905	Intermediate Similarity	NPC217673
0.7902	Intermediate Similarity	NPC472706
0.7898	Intermediate Similarity	NPC228204
0.7898	Intermediate Similarity	NPC112523
0.7898	Intermediate Similarity	NPC114410
0.7898	Intermediate Similarity	NPC472549
0.7898	Intermediate Similarity	NPC26033
0.7881	Intermediate Similarity	NPC182869
0.7881	Intermediate Similarity	NPC63737
0.7877	Intermediate Similarity	NPC472394
0.7871	Intermediate Similarity	NPC198455
0.7871	Intermediate Similarity	NPC161239
0.7871	Intermediate Similarity	NPC165260
0.7867	Intermediate Similarity	NPC477904
0.7867	Intermediate Similarity	NPC183270
0.7867	Intermediate Similarity	NPC87934
0.7867	Intermediate Similarity	NPC162613
0.7857	Intermediate Similarity	NPC132652
0.7847	Intermediate Similarity	NPC472707
0.7834	Intermediate Similarity	NPC219419
0.7829	Intermediate Similarity	NPC477894
0.7826	Intermediate Similarity	NPC43304
0.7826	Intermediate Similarity	NPC477190
0.7826	Intermediate Similarity	NPC477188
0.7821	Intermediate Similarity	NPC96308
0.7817	Intermediate Similarity	NPC472704
0.7806	Intermediate Similarity	NPC76103
0.78	Intermediate Similarity	NPC9905
0.7799	Intermediate Similarity	NPC469771
0.7792	Intermediate Similarity	NPC312393
0.7792	Intermediate Similarity	NPC477737
0.7791	Intermediate Similarity	NPC324769
0.7791	Intermediate Similarity	NPC61891
0.7791	Intermediate Similarity	NPC325732
0.7791	Intermediate Similarity	NPC477491
0.7786	Intermediate Similarity	NPC473243
0.7785	Intermediate Similarity	NPC114357
0.7785	Intermediate Similarity	NPC473611
0.7785	Intermediate Similarity	NPC155329
0.7785	Intermediate Similarity	NPC259144
0.7771	Intermediate Similarity	NPC472548
0.7771	Intermediate Similarity	NPC477905
0.7764	Intermediate Similarity	NPC329997
0.7763	Intermediate Similarity	NPC472546
0.7763	Intermediate Similarity	NPC192658
0.7756	Intermediate Similarity	NPC473214
0.7756	Intermediate Similarity	NPC470245
0.7755	Intermediate Similarity	NPC469499
0.7755	Intermediate Similarity	NPC238370
0.7755	Intermediate Similarity	NPC475569
0.7748	Intermediate Similarity	NPC43241
0.7748	Intermediate Similarity	NPC473081
0.7748	Intermediate Similarity	NPC147880
0.7748	Intermediate Similarity	NPC473109
0.7748	Intermediate Similarity	NPC211137
0.7748	Intermediate Similarity	NPC48017
0.7748	Intermediate Similarity	NPC473060

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 NPC477095 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	831
0.2-0.3	1756
0.3-0.4	3092
0.4-0.5	2157
0.5-0.6	842
0.6-0.7	146
0.7-0.8	7
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
0.7927	Intermediate Similarity	NPD7799	Discontinued
0.7843	Intermediate Similarity	NPD7236	Approved
0.7707	Intermediate Similarity	NPD7239	Suspended
0.7584	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7058	Phase 2
0.7273	Intermediate Similarity	NPD7057	Phase 3
0.7225	Intermediate Similarity	NPD7685	Pre-registration
0.7126	Intermediate Similarity	NPD8368	Discontinued
0.7102	Intermediate Similarity	NPD8407	Phase 2
0.7073	Intermediate Similarity	NPD6599	Discontinued
0.7071	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8434	Phase 2
0.7007	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2067	Discontinued
0.6948	Remote Similarity	NPD7961	Discontinued
0.6946	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD8435	Approved
0.6937	Remote Similarity	NPD4628	Phase 3
0.6929	Remote Similarity	NPD2182	Approved
0.6928	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7075	Discontinued
0.6914	Remote Similarity	NPD6799	Approved
0.6882	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD8360	Approved
0.6851	Remote Similarity	NPD8361	Approved
0.6846	Remote Similarity	NPD6287	Discontinued
0.6824	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6801	Discontinued
0.6759	Remote Similarity	NPD2629	Approved
0.6746	Remote Similarity	NPD5761	Phase 2
0.6746	Remote Similarity	NPD5760	Phase 2
0.6742	Remote Similarity	NPD6765	Approved
0.6742	Remote Similarity	NPD6764	Approved
0.674	Remote Similarity	NPD8150	Discontinued
0.6736	Remote Similarity	NPD7094	Approved
0.6736	Remote Similarity	NPD6858	Approved
0.6732	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6085	Phase 2
0.672	Remote Similarity	NPD8485	Approved
0.6715	Remote Similarity	NPD1238	Approved
0.6712	Remote Similarity	NPD4198	Discontinued
0.6706	Remote Similarity	NPD3817	Phase 2
0.6706	Remote Similarity	NPD5402	Approved
0.6689	Remote Similarity	NPD7741	Discontinued
0.6687	Remote Similarity	NPD3887	Approved
0.6687	Remote Similarity	NPD6190	Approved
0.6687	Remote Similarity	NPD5403	Approved
0.6685	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD6685	Approved
0.6647	Remote Similarity	NPD7819	Suspended
0.6646	Remote Similarity	NPD6355	Discontinued
0.6645	Remote Similarity	NPD6832	Phase 2
0.6643	Remote Similarity	NPD164	Approved
0.6614	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD5667	Approved
0.6595	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6785	Approved
0.6593	Remote Similarity	NPD6784	Approved
0.6584	Remote Similarity	NPD2796	Approved
0.6573	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3764	Approved
0.6552	Remote Similarity	NPD5494	Approved
0.6552	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD6273	Approved
0.6497	Remote Similarity	NPD7008	Discontinued
0.6494	Remote Similarity	NPD1876	Approved
0.6488	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD5048	Discontinued
0.6474	Remote Similarity	NPD3882	Suspended
0.6471	Remote Similarity	NPD3972	Approved
0.6471	Remote Similarity	NPD4380	Phase 2
0.6454	Remote Similarity	NPD5765	Approved
0.6442	Remote Similarity	NPD6002	Phase 3
0.6442	Remote Similarity	NPD6005	Phase 3
0.6442	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5762	Approved
0.6442	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5763	Approved
0.6442	Remote Similarity	NPD2353	Approved
0.6442	Remote Similarity	NPD6004	Phase 3
0.6438	Remote Similarity	NPD6912	Phase 3
0.6424	Remote Similarity	NPD2575	Approved
0.642	Remote Similarity	NPD7033	Discontinued
0.642	Remote Similarity	NPD8127	Discontinued
0.642	Remote Similarity	NPD2799	Discontinued
0.642	Remote Similarity	NPD7305	Phase 1
0.6416	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7713	Phase 3
0.6414	Remote Similarity	NPD8462	Phase 1
0.6412	Remote Similarity	NPD7458	Discontinued
0.641	Remote Similarity	NPD5647	Approved
0.6408	Remote Similarity	NPD1237	Approved
0.6404	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.64	Remote Similarity	NPD919	Approved
0.6391	Remote Similarity	NPD920	Approved
0.6387	Remote Similarity	NPD8285	Discontinued
0.6382	Remote Similarity	NPD17	Approved
0.638	Remote Similarity	NPD7137	Phase 2
0.6369	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD7473	Discontinued
0.6364	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD2569	Approved
0.6358	Remote Similarity	NPD2567	Approved
0.6358	Remote Similarity	NPD9545	Approved
0.6357	Remote Similarity	NPD7798	Approved
0.6352	Remote Similarity	NPD2313	Discontinued
0.6348	Remote Similarity	NPD3926	Phase 2
0.6345	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD1471	Phase 3
0.6341	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD1930	Approved
0.6338	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD1929	Approved
0.6337	Remote Similarity	NPD6386	Approved
0.6337	Remote Similarity	NPD6385	Approved
0.6337	Remote Similarity	NPD7411	Suspended
0.6333	Remote Similarity	NPD3751	Discontinued
0.6333	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5585	Approved
0.6316	Remote Similarity	NPD3226	Approved
0.6309	Remote Similarity	NPD5951	Approved
0.6308	Remote Similarity	NPD8320	Phase 1
0.6308	Remote Similarity	NPD8319	Approved
0.6306	Remote Similarity	NPD2798	Approved
0.6304	Remote Similarity	NPD8313	Approved
0.6304	Remote Similarity	NPD8312	Approved
0.6299	Remote Similarity	NPD4807	Approved
0.6299	Remote Similarity	NPD4806	Approved
0.6296	Remote Similarity	NPD6653	Approved
0.6292	Remote Similarity	NPD3787	Discontinued
0.6287	Remote Similarity	NPD2354	Approved
0.6286	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5305	Approved
0.6275	Remote Similarity	NPD5306	Approved
0.6272	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD6637	Approved
0.6258	Remote Similarity	NPD1608	Approved
0.6257	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD7497	Discontinued
0.625	Remote Similarity	NPD6319	Approved
0.625	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7808	Phase 3
0.6243	Remote Similarity	NPD3818	Discontinued
0.6242	Remote Similarity	NPD2346	Discontinued
0.6236	Remote Similarity	NPD1247	Approved
0.6235	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD230	Phase 1
0.6235	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD4135	Approved
0.6234	Remote Similarity	NPD4106	Approved
0.6234	Remote Similarity	NPD4136	Approved
0.6232	Remote Similarity	NPD1202	Approved
0.623	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD7055	Discontinued
0.6224	Remote Similarity	NPD6647	Phase 2
0.6222	Remote Similarity	NPD6166	Phase 2
0.6222	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.622	Remote Similarity	NPD3748	Approved
0.622	Remote Similarity	NPD1510	Phase 2
0.6211	Remote Similarity	NPD8032	Phase 2
0.6211	Remote Similarity	NPD6233	Phase 2
0.6211	Remote Similarity	NPD6663	Approved
0.6207	Remote Similarity	NPD1934	Approved
0.6205	Remote Similarity	NPD1549	Phase 2
0.6201	Remote Similarity	NPD6232	Discontinued
0.6196	Remote Similarity	NPD7251	Discontinued
0.6194	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD7768	Phase 2
0.6188	Remote Similarity	NPD6039	Approved
0.6188	Remote Similarity	NPD7095	Approved
0.6182	Remote Similarity	NPD2438	Suspended
0.6182	Remote Similarity	NPD2935	Discontinued
0.6181	Remote Similarity	NPD5909	Discontinued
0.6176	Remote Similarity	NPD2534	Approved
0.6176	Remote Similarity	NPD2533	Approved
0.6176	Remote Similarity	NPD2532	Approved
0.6176	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD7435	Discontinued
0.6173	Remote Similarity	NPD1240	Approved
0.6171	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD5126	Approved
0.6169	Remote Similarity	NPD5125	Phase 3
0.6168	Remote Similarity	NPD1243	Approved
0.6167	Remote Similarity	NPD5242	Approved
0.6166	Remote Similarity	NPD7699	Phase 2
0.6166	Remote Similarity	NPD7700	Phase 2

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