NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	616.27
Volume:	629.984
LogP:	5.034
LogD:	4.391
LogS:	-3.994
# Rotatable Bonds:	8
TPSA:	128.73
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.22
Synthetic Accessibility Score:	5.477
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:	-5.142
MDCK Permeability:	3.314439163659699e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.08
20% Bioavailability (F20%):	0.966
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	98.67581176757812%
Volume Distribution (VD):	2.238
Pgp-substrate:	7.734283924102783%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.063
CYP2C19-inhibitor:	0.246
CYP2C19-substrate:	0.318
CYP2C9-inhibitor:	0.911
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.924
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.952
CYP3A4-substrate:	0.772

ADMET: Excretion

Clearance (CL):	10.309
Half-life (T1/2):	0.194

ADMET: Toxicity

hERG Blockers:	0.363
Human Hepatotoxicity (H-HT):	0.782
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.842
Maximum Recommended Daily Dose:	0.057
Skin Sensitization:	0.18
Carcinogencity:	0.063
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC477100

Natural Product ID:	NPC477100
*Common Name:**	(1aR,2S,3R,4aR,6R,7S,7aS,8E,10R,11S,11aS)-1,1,3,6,9-Pentamethyl-2-acetoxy-4a,7a-epoxy-7,11-bis(benzoyloxy)-10-hydroxy-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,14R)-4-acetyloxy-13-benzoyloxy-9-hydroxy-3,6,6,10,14-pentamethyl-2-oxo-16-oxatetracyclo[10.3.1.01,12.05,7]hexadec-10-en-8-yl] benzoate
Synonyms:
Standard InCHIKey:	CYKBATSQYYKRDV-CEJPBEFTSA-N
Standard InCHI:	InChI=1S/C36H40O9/c1-19-17-36-31(44-33(41)24-15-11-8-12-16-24)20(2)18-35(36,45-36)30(39)21(3)28(42-22(4)37)25-26(34(25,5)6)29(27(19)38)43-32(40)23-13-9-7-10-14-23/h7-17,20-21,25-29,31,38H,18H2,1-6H3/b19-17+/t20-,21-,25+,26-,27-,28-,29+,31+,35+,36+/m1/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)O)OC(=O)C6=CC=CC=C6)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44179573
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	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	IC50	>	5	ug/ml	PMID[19438253]
NPT2	Others	Unspecified	Inhibition	=	1.1	%	PMID[19438253]
NPT2	Others	Unspecified	Inhibition	=	1.8	%	PMID[19438253]
NPT2	Others	Unspecified	Inhibition	=	3.6	%	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 NPC477100 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	333
0.1-0.2	1112
0.2-0.3	2639
0.3-0.4	6034
0.4-0.5	11492
0.5-0.6	11922
0.6-0.7	8199
0.7-0.8	793
0.8-0.85	66
0.85-0.9	64
0.9-0.95	29
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477098
0.979	High Similarity	NPC477101
0.979	High Similarity	NPC477097
0.979	High Similarity	NPC25484
0.979	High Similarity	NPC232583
0.979	High Similarity	NPC477099
0.965	High Similarity	NPC205389
0.958	High Similarity	NPC477095
0.9371	High Similarity	NPC82467
0.9371	High Similarity	NPC477096
0.9371	High Similarity	NPC477094
0.9371	High Similarity	NPC45307
0.9231	High Similarity	NPC475413
0.9231	High Similarity	NPC473497
0.9231	High Similarity	NPC474303
0.9231	High Similarity	NPC473654
0.9231	High Similarity	NPC242355
0.9161	High Similarity	NPC475660
0.9091	High Similarity	NPC272523
0.9091	High Similarity	NPC325805
0.9091	High Similarity	NPC473301
0.9091	High Similarity	NPC276652
0.9048	High Similarity	NPC170668
0.9021	High Similarity	NPC86772
0.8951	High Similarity	NPC285221
0.8951	High Similarity	NPC194769
0.8951	High Similarity	NPC477358
0.8881	High Similarity	NPC79699
0.8881	High Similarity	NPC270364
0.8881	High Similarity	NPC290833
0.8881	High Similarity	NPC265459
0.8881	High Similarity	NPC477367
0.8881	High Similarity	NPC232888
0.8881	High Similarity	NPC475262
0.8881	High Similarity	NPC472247
0.8851	High Similarity	NPC134131
0.8851	High Similarity	NPC25043
0.8811	High Similarity	NPC477368
0.8811	High Similarity	NPC472250
0.8811	High Similarity	NPC477359
0.8811	High Similarity	NPC311492
0.8811	High Similarity	NPC28836
0.8811	High Similarity	NPC153617
0.8759	High Similarity	NPC27721
0.8742	High Similarity	NPC125033
0.8741	High Similarity	NPC477364
0.8741	High Similarity	NPC472248
0.8716	High Similarity	NPC153214
0.869	High Similarity	NPC202729
0.8671	High Similarity	NPC233860
0.8671	High Similarity	NPC239358
0.8671	High Similarity	NPC233692
0.8671	High Similarity	NPC477360
0.8662	High Similarity	NPC55744
0.8621	High Similarity	NPC200154
0.8581	High Similarity	NPC187566
0.8581	High Similarity	NPC11410
0.8531	High Similarity	NPC122504
0.8531	High Similarity	NPC272946
0.8531	High Similarity	NPC475671
0.8531	High Similarity	NPC42234
0.8531	High Similarity	NPC475452
0.8531	High Similarity	NPC3450
0.8516	High Similarity	NPC251139
0.8514	High Similarity	NPC251294
0.8462	Intermediate Similarity	NPC37968
0.8462	Intermediate Similarity	NPC70344
0.8397	Intermediate Similarity	NPC21410
0.8397	Intermediate Similarity	NPC473670
0.8392	Intermediate Similarity	NPC477370
0.8387	Intermediate Similarity	NPC283875
0.8387	Intermediate Similarity	NPC138641
0.8387	Intermediate Similarity	NPC469647
0.8387	Intermediate Similarity	NPC22571
0.8387	Intermediate Similarity	NPC469648
0.8344	Intermediate Similarity	NPC95449
0.8344	Intermediate Similarity	NPC106895
0.8323	Intermediate Similarity	NPC51602
0.8323	Intermediate Similarity	NPC471103
0.8322	Intermediate Similarity	NPC477357
0.8322	Intermediate Similarity	NPC121268
0.8322	Intermediate Similarity	NPC477365
0.8322	Intermediate Similarity	NPC53361
0.8311	Intermediate Similarity	NPC217673
0.8311	Intermediate Similarity	NPC52523
0.8282	Intermediate Similarity	NPC40138
0.828	Intermediate Similarity	NPC469456
0.828	Intermediate Similarity	NPC282239
0.8276	Intermediate Similarity	NPC475508
0.8269	Intermediate Similarity	NPC233581
0.8269	Intermediate Similarity	NPC145649
0.8258	Intermediate Similarity	NPC7095
0.8255	Intermediate Similarity	NPC327511
0.8255	Intermediate Similarity	NPC205305
0.8252	Intermediate Similarity	NPC477363
0.8252	Intermediate Similarity	NPC477366
0.8243	Intermediate Similarity	NPC279637
0.8243	Intermediate Similarity	NPC149401
0.8235	Intermediate Similarity	NPC127857
0.8235	Intermediate Similarity	NPC471162
0.8228	Intermediate Similarity	NPC217091
0.8217	Intermediate Similarity	NPC237549
0.8217	Intermediate Similarity	NPC1173
0.8217	Intermediate Similarity	NPC472030
0.8217	Intermediate Similarity	NPC265395
0.8217	Intermediate Similarity	NPC473414
0.8217	Intermediate Similarity	NPC257213
0.8217	Intermediate Similarity	NPC242262
0.8217	Intermediate Similarity	NPC256142
0.8217	Intermediate Similarity	NPC472022
0.8217	Intermediate Similarity	NPC304876
0.8217	Intermediate Similarity	NPC472005
0.8217	Intermediate Similarity	NPC158333
0.8217	Intermediate Similarity	NPC249471
0.8205	Intermediate Similarity	NPC472398
0.8194	Intermediate Similarity	NPC60509
0.8194	Intermediate Similarity	NPC250046
0.8194	Intermediate Similarity	NPC81698
0.8182	Intermediate Similarity	NPC312393
0.8176	Intermediate Similarity	NPC134937
0.8176	Intermediate Similarity	NPC298547
0.8176	Intermediate Similarity	NPC472393
0.8176	Intermediate Similarity	NPC324898
0.8165	Intermediate Similarity	NPC114410
0.8165	Intermediate Similarity	NPC472549
0.8165	Intermediate Similarity	NPC114357
0.8165	Intermediate Similarity	NPC259144
0.8165	Intermediate Similarity	NPC155329
0.8165	Intermediate Similarity	NPC228204
0.8165	Intermediate Similarity	NPC26033
0.8165	Intermediate Similarity	NPC112523
0.8158	Intermediate Similarity	NPC475135
0.8158	Intermediate Similarity	NPC192658
0.8158	Intermediate Similarity	NPC182869
0.8146	Intermediate Similarity	NPC87934
0.8146	Intermediate Similarity	NPC162613
0.8141	Intermediate Similarity	NPC112216
0.8141	Intermediate Similarity	NPC198455
0.8141	Intermediate Similarity	NPC165260
0.8141	Intermediate Similarity	NPC161239
0.8138	Intermediate Similarity	NPC472707
0.8129	Intermediate Similarity	NPC132652
0.8125	Intermediate Similarity	NPC471102
0.8112	Intermediate Similarity	NPC8990
0.8112	Intermediate Similarity	NPC477362
0.8105	Intermediate Similarity	NPC131966
0.8105	Intermediate Similarity	NPC191387
0.8105	Intermediate Similarity	NPC477894
0.8101	Intermediate Similarity	NPC248265
0.8101	Intermediate Similarity	NPC219419
0.8101	Intermediate Similarity	NPC134685
0.8101	Intermediate Similarity	NPC11588
0.8101	Intermediate Similarity	NPC229545
0.8101	Intermediate Similarity	NPC77719
0.8089	Intermediate Similarity	NPC101043
0.8089	Intermediate Similarity	NPC306799
0.8089	Intermediate Similarity	NPC470153
0.8086	Intermediate Similarity	NPC477190
0.8086	Intermediate Similarity	NPC43304
0.8086	Intermediate Similarity	NPC477188
0.8079	Intermediate Similarity	NPC9905
0.8069	Intermediate Similarity	NPC472706
0.8065	Intermediate Similarity	NPC477737
0.8063	Intermediate Similarity	NPC469771
0.8056	Intermediate Similarity	NPC477369
0.8052	Intermediate Similarity	NPC34943
0.805	Intermediate Similarity	NPC132599
0.805	Intermediate Similarity	NPC473611
0.805	Intermediate Similarity	NPC473632
0.805	Intermediate Similarity	NPC469730
0.8049	Intermediate Similarity	NPC477491
0.8049	Intermediate Similarity	NPC61891
0.8049	Intermediate Similarity	NPC324769
0.8049	Intermediate Similarity	NPC325732
0.8039	Intermediate Similarity	NPC63737
0.8039	Intermediate Similarity	NPC183540
0.8038	Intermediate Similarity	NPC472548
0.8038	Intermediate Similarity	NPC477905
0.8026	Intermediate Similarity	NPC473440
0.8025	Intermediate Similarity	NPC473214
0.8025	Intermediate Similarity	NPC470245
0.8025	Intermediate Similarity	NPC254558
0.8025	Intermediate Similarity	NPC329997
0.8013	Intermediate Similarity	NPC327031
0.8	Intermediate Similarity	NPC471107
0.8	Intermediate Similarity	NPC471100
0.8	Intermediate Similarity	NPC122491
0.8	Intermediate Similarity	NPC161151
0.8	Intermediate Similarity	NPC32
0.7988	Intermediate Similarity	NPC471134
0.7975	Intermediate Similarity	NPC197037
0.7974	Intermediate Similarity	NPC266374
0.7962	Intermediate Similarity	NPC476975
0.7962	Intermediate Similarity	NPC473215
0.7949	Intermediate Similarity	NPC240115
0.7949	Intermediate Similarity	NPC478263
0.7949	Intermediate Similarity	NPC20255
0.7927	Intermediate Similarity	NPC66193
0.7922	Intermediate Similarity	NPC472546
0.7914	Intermediate Similarity	NPC476077

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 NPC477100 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	768
0.2-0.3	1783
0.3-0.4	2935
0.4-0.5	2250
0.5-0.6	889
0.6-0.7	239
0.7-0.8	10
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
0.8072	Intermediate Similarity	NPD7799	Discontinued
0.8	Intermediate Similarity	NPD7236	Approved
0.7867	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD7239	Suspended
0.7584	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7685	Pre-registration
0.7425	Intermediate Similarity	NPD7057	Phase 3
0.7425	Intermediate Similarity	NPD7058	Phase 2
0.7371	Intermediate Similarity	NPD8368	Discontinued
0.736	Intermediate Similarity	NPD8434	Phase 2
0.7345	Intermediate Similarity	NPD8407	Phase 2
0.7312	Intermediate Similarity	NPD4628	Phase 3
0.7263	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8361	Approved
0.7182	Intermediate Similarity	NPD8360	Approved
0.7182	Intermediate Similarity	NPD8435	Approved
0.7176	Intermediate Similarity	NPD7075	Discontinued
0.7172	Intermediate Similarity	NPD2629	Approved
0.7126	Intermediate Similarity	NPD6599	Discontinued
0.7101	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8150	Discontinued
0.7055	Intermediate Similarity	NPD6190	Approved
0.7055	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD8485	Approved
0.7041	Intermediate Similarity	NPD6801	Discontinued
0.7013	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6085	Phase 2
0.7006	Intermediate Similarity	NPD7961	Discontinued
0.7	Intermediate Similarity	NPD5761	Phase 2
0.7	Intermediate Similarity	NPD5760	Phase 2
0.698	Remote Similarity	NPD7741	Discontinued
0.697	Remote Similarity	NPD6799	Approved
0.6959	Remote Similarity	NPD5402	Approved
0.6946	Remote Similarity	NPD5403	Approved
0.6931	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4198	Discontinued
0.6889	Remote Similarity	NPD6764	Approved
0.6889	Remote Similarity	NPD6765	Approved
0.6853	Remote Similarity	NPD6685	Approved
0.6826	Remote Similarity	NPD5401	Approved
0.6826	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4380	Phase 2
0.6816	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6355	Discontinued
0.6795	Remote Similarity	NPD5647	Approved
0.6788	Remote Similarity	NPD2575	Approved
0.6783	Remote Similarity	NPD5048	Discontinued
0.6781	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3817	Phase 2
0.6739	Remote Similarity	NPD6784	Approved
0.6739	Remote Similarity	NPD6785	Approved
0.6732	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3764	Approved
0.6724	Remote Similarity	NPD3882	Suspended
0.6713	Remote Similarity	NPD1237	Approved
0.6712	Remote Similarity	NPD2067	Discontinued
0.6707	Remote Similarity	NPD6004	Phase 3
0.6707	Remote Similarity	NPD6002	Phase 3
0.6707	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5762	Approved
0.6707	Remote Similarity	NPD6005	Phase 3
0.6707	Remote Similarity	NPD5763	Approved
0.6707	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7819	Suspended
0.6687	Remote Similarity	NPD7305	Phase 1
0.6687	Remote Similarity	NPD7033	Discontinued
0.6686	Remote Similarity	NPD6273	Approved
0.6686	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD3751	Discontinued
0.6667	Remote Similarity	NPD6653	Approved
0.6648	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7137	Phase 2
0.6644	Remote Similarity	NPD2182	Approved
0.6643	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD5765	Approved
0.6633	Remote Similarity	NPD8462	Phase 1
0.663	Remote Similarity	NPD8312	Approved
0.663	Remote Similarity	NPD8313	Approved
0.6627	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD6912	Phase 3
0.6615	Remote Similarity	NPD8320	Phase 1
0.6615	Remote Similarity	NPD8319	Approved
0.6606	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6287	Discontinued
0.6581	Remote Similarity	NPD4806	Approved
0.6581	Remote Similarity	NPD4807	Approved
0.6576	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD7808	Phase 3
0.6575	Remote Similarity	NPD3818	Discontinued
0.6573	Remote Similarity	NPD8127	Discontinued
0.6571	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7458	Discontinued
0.6558	Remote Similarity	NPD5305	Approved
0.6558	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD5306	Approved
0.6557	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6166	Phase 2
0.6536	Remote Similarity	NPD6319	Approved
0.6536	Remote Similarity	NPD9545	Approved
0.6536	Remote Similarity	NPD3787	Discontinued
0.6534	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6647	Phase 2
0.6527	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7251	Discontinued
0.6519	Remote Similarity	NPD7473	Discontinued
0.6516	Remote Similarity	NPD4136	Approved
0.6516	Remote Similarity	NPD4135	Approved
0.6516	Remote Similarity	NPD4106	Approved
0.6503	Remote Similarity	NPD230	Phase 1
0.6494	Remote Similarity	NPD7411	Suspended
0.649	Remote Similarity	NPD5951	Approved
0.6486	Remote Similarity	NPD6371	Approved
0.6485	Remote Similarity	NPD2799	Discontinued
0.648	Remote Similarity	NPD7435	Discontinued
0.6477	Remote Similarity	NPD7699	Phase 2
0.6477	Remote Similarity	NPD7700	Phase 2
0.6474	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD3226	Approved
0.6467	Remote Similarity	NPD6858	Approved
0.6467	Remote Similarity	NPD6797	Phase 2
0.6467	Remote Similarity	NPD7094	Approved
0.6457	Remote Similarity	NPD1934	Approved
0.6452	Remote Similarity	NPD5125	Phase 3
0.6452	Remote Similarity	NPD5126	Approved
0.645	Remote Similarity	NPD3887	Approved
0.645	Remote Similarity	NPD2354	Approved
0.6438	Remote Similarity	NPD5204	Approved
0.6434	Remote Similarity	NPD1238	Approved
0.6422	Remote Similarity	NPD8404	Phase 2
0.642	Remote Similarity	NPD2313	Discontinued
0.642	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD1929	Approved
0.6414	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD1930	Approved
0.6413	Remote Similarity	NPD7074	Phase 3
0.6409	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6535	Approved
0.6406	Remote Similarity	NPD6534	Approved
0.6398	Remote Similarity	NPD6832	Phase 2
0.6396	Remote Similarity	NPD7497	Discontinued
0.6391	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD8166	Discontinued
0.6387	Remote Similarity	NPD4105	Approved
0.6387	Remote Similarity	NPD4102	Approved
0.6386	Remote Similarity	NPD1510	Phase 2
0.638	Remote Similarity	NPD6233	Phase 2
0.638	Remote Similarity	NPD6663	Approved
0.6374	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.637	Remote Similarity	NPD164	Approved
0.6369	Remote Similarity	NPD1549	Phase 2
0.6368	Remote Similarity	NPD7874	Approved
0.6368	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD9495	Approved
0.6359	Remote Similarity	NPD7054	Approved
0.6358	Remote Similarity	NPD7095	Approved
0.6354	Remote Similarity	NPD6232	Discontinued
0.6352	Remote Similarity	NPD5667	Approved
0.6348	Remote Similarity	NPD7768	Phase 2
0.6347	Remote Similarity	NPD2935	Discontinued
0.6347	Remote Similarity	NPD2796	Approved
0.6344	Remote Similarity	NPD6559	Discontinued
0.6341	Remote Similarity	NPD1240	Approved
0.634	Remote Similarity	NPD7115	Discovery
0.634	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD2534	Approved
0.6337	Remote Similarity	NPD2532	Approved
0.6337	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD2533	Approved
0.6335	Remote Similarity	NPD3662	Phase 3
0.6335	Remote Similarity	NPD3664	Approved
0.6335	Remote Similarity	NPD5736	Approved
0.6335	Remote Similarity	NPD3661	Approved
0.6335	Remote Similarity	NPD3663	Approved
0.6333	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5494	Approved
0.6329	Remote Similarity	NPD1608	Approved
0.6328	Remote Similarity	NPD2801	Approved
0.6324	Remote Similarity	NPD7472	Approved
0.6319	Remote Similarity	NPD6798	Discontinued
0.6313	Remote Similarity	NPD3749	Approved
0.6312	Remote Similarity	NPD6362	Approved
0.631	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.631	Remote Similarity	NPD2346	Discontinued
0.631	Remote Similarity	NPD7266	Discontinued
0.631	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4684	Phase 3
0.6303	Remote Similarity	NPD4686	Approved
0.6303	Remote Similarity	NPD4685	Phase 3
0.6298	Remote Similarity	NPD7199	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