NPASS Compound

Structure

NPC476071 OpenBabel07101718332D 34 38 0 0 1 0 0 0 0 0999 V2000 -3.3753 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5058 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0186 -0.6177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1935 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6876 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5315 -2.4359 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5315 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5315 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2191 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5315 1.4615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3753 -2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7063 -0.3566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 5 27 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 26 1 0 0 0 0 13 28 1 0 0 0 0 14 16 1 0 0 0 0 14 27 1 0 0 0 0 15 17 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 30 1 0 0 0 0 18 23 1 0 0 0 0 18 29 1 1 0 0 0 19 23 1 0 0 0 0 19 27 1 6 0 0 0 20 25 1 0 0 0 0 20 26 1 1 0 0 0 21 26 1 1 0 0 0 21 28 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 1 0 0 0 23 30 1 6 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 26 4 1 1 0 0 0 27 28 1 1 0 0 0 28 6 1 1 0 0 0 29 7 1 1 0 0 0 29 34 1 0 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.37
Volume:	517.178
LogP:	4.613
LogD:	4.861
LogS:	-3.793
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.418
Synthetic Accessibility Score:	4.888
Fsp3:	0.967
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.363
MDCK Permeability:	6.330268661258742e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.142
30% Bioavailability (F30%):	0.894

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	92.299560546875%
Volume Distribution (VD):	0.844
Pgp-substrate:	2.6552135944366455%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.476
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.93
CYP2C9-inhibitor:	0.151
CYP2C9-substrate:	0.884
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.46
CYP3A4-inhibitor:	0.1
CYP3A4-substrate:	0.146

ADMET: Excretion

Clearance (CL):	2.316
Half-life (T1/2):	0.339

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.145
Drug-inuced Liver Injury (DILI):	0.008
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.067
Maximum Recommended Daily Dose:	0.87
Skin Sensitization:	0.728
Carcinogencity:	0.003
Eye Corrosion:	0.933
Eye Irritation:	0.913
Respiratory Toxicity:	0.754

Download Data

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

Natural Product: NPC476071

Natural Product ID:	NPC476071
*Common Name:**	Oleanderic Acid
IUPAC Name:	(1R,2R,4aR,6aR,6aR,6bR,8aR,10S,12aR,14aR,14bR)-2,10-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14,14a,14b-hexadecahydropicene-4a-carboxylic acid
Synonyms:	oleanderic acid
Standard InCHIKey:	WJCIWKNYROGCFD-XOVAVQBPSA-N
Standard InCHI:	InChI=1S/C30H50O4/c1-18-23-19-8-9-21-26(4)12-11-22(31)25(2,3)20(26)10-13-28(21,6)27(19,5)14-16-30(23,24(32)33)17-15-29(18,7)34/h18-23,31,34H,8-17H2,1-7H3,(H,32,33)/t18-,19-,20+,21-,22+,23+,26+,27-,28-,29-,30-/m1/s1
SMILES:	CC1C2C3CCC4C5(CCC(C(C5CCC4(C3(CCC2(CCC1(C)O)C(=O)O)C)C)(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL524527
PubChem CID:	44583857
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	Niigata City, Niigata Province, Japan	2000-Nov	PMID[15730243]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933868]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253842]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	n.a.	n.a.	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	Niigata City, Niigata Province, Japan	2001-NOV	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29693393]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	Leaves; Stems	n.a.	n.a.	PMID[9214727]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10021	Nerium oleander	Species	Apocynaceae	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	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	>	212000.0	nM	PMID[509907]
NPT27	Others	Unspecified		IC50	=	3400.0	nM	PMID[509907]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	159000.0	nM	PMID[509907]

☑ 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 NPC476071 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	472
0.1-0.2	3480
0.2-0.3	10909
0.3-0.4	13478
0.4-0.5	5809
0.5-0.6	4645
0.6-0.7	2861
0.7-0.8	951
0.8-0.85	60
0.85-0.9	28
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9211	High Similarity	NPC112463
0.9091	High Similarity	NPC472608
0.8929	High Similarity	NPC185529
0.8929	High Similarity	NPC472146
0.8889	High Similarity	NPC219535
0.8889	High Similarity	NPC237938
0.8846	High Similarity	NPC26029
0.8846	High Similarity	NPC31031
0.8846	High Similarity	NPC243594
0.875	High Similarity	NPC280781
0.875	High Similarity	NPC48756
0.8684	High Similarity	NPC68426
0.8684	High Similarity	NPC477229
0.8684	High Similarity	NPC282905
0.8675	High Similarity	NPC83242
0.8642	High Similarity	NPC268040
0.8608	High Similarity	NPC171426
0.8608	High Similarity	NPC324700
0.8608	High Similarity	NPC224802
0.8608	High Similarity	NPC34046
0.8608	High Similarity	NPC80089
0.859	High Similarity	NPC108840
0.8571	High Similarity	NPC159325
0.8571	High Similarity	NPC168511
0.8554	High Similarity	NPC131350
0.8554	High Similarity	NPC62572
0.8523	High Similarity	NPC82633
0.85	High Similarity	NPC201276
0.85	High Similarity	NPC320144
0.85	High Similarity	NPC80891
0.8481	Intermediate Similarity	NPC298168
0.8481	Intermediate Similarity	NPC143133
0.8471	Intermediate Similarity	NPC473319
0.8471	Intermediate Similarity	NPC131104
0.8471	Intermediate Similarity	NPC3032
0.8462	Intermediate Similarity	NPC267753
0.8452	Intermediate Similarity	NPC472272
0.8434	Intermediate Similarity	NPC473299
0.8427	Intermediate Similarity	NPC235109
0.8427	Intermediate Similarity	NPC163685
0.8415	Intermediate Similarity	NPC61107
0.8415	Intermediate Similarity	NPC289486
0.8415	Intermediate Similarity	NPC30583
0.8395	Intermediate Similarity	NPC477851
0.8375	Intermediate Similarity	NPC185465
0.8372	Intermediate Similarity	NPC67653
0.8372	Intermediate Similarity	NPC471459
0.8354	Intermediate Similarity	NPC4209
0.8333	Intermediate Similarity	NPC130011
0.8293	Intermediate Similarity	NPC271572
0.8293	Intermediate Similarity	NPC474870
0.8276	Intermediate Similarity	NPC18536
0.8276	Intermediate Similarity	NPC50443
0.8276	Intermediate Similarity	NPC475211
0.8276	Intermediate Similarity	NPC88337
0.8272	Intermediate Similarity	NPC73013
0.825	Intermediate Similarity	NPC207010
0.825	Intermediate Similarity	NPC317913
0.825	Intermediate Similarity	NPC221420
0.8242	Intermediate Similarity	NPC472144
0.8235	Intermediate Similarity	NPC187545
0.8235	Intermediate Similarity	NPC248216
0.8235	Intermediate Similarity	NPC302111
0.8228	Intermediate Similarity	NPC159789
0.8228	Intermediate Similarity	NPC212733
0.8214	Intermediate Similarity	NPC477434
0.8214	Intermediate Similarity	NPC105895
0.8205	Intermediate Similarity	NPC81759
0.8193	Intermediate Similarity	NPC121121
0.8171	Intermediate Similarity	NPC261616
0.8161	Intermediate Similarity	NPC56962
0.8161	Intermediate Similarity	NPC24705
0.8158	Intermediate Similarity	NPC180777
0.8158	Intermediate Similarity	NPC103647
0.8158	Intermediate Similarity	NPC260319
0.8158	Intermediate Similarity	NPC100917
0.8158	Intermediate Similarity	NPC281203
0.8158	Intermediate Similarity	NPC469724
0.8158	Intermediate Similarity	NPC31187
0.8158	Intermediate Similarity	NPC2568
0.814	Intermediate Similarity	NPC470920
0.8132	Intermediate Similarity	NPC472145
0.8125	Intermediate Similarity	NPC475742
0.8125	Intermediate Similarity	NPC474020
0.8125	Intermediate Similarity	NPC5767
0.8111	Intermediate Similarity	NPC473240
0.8101	Intermediate Similarity	NPC167702
0.8101	Intermediate Similarity	NPC280026
0.8095	Intermediate Similarity	NPC269684
0.809	Intermediate Similarity	NPC472148
0.809	Intermediate Similarity	NPC472147
0.809	Intermediate Similarity	NPC224060
0.809	Intermediate Similarity	NPC244356
0.8077	Intermediate Similarity	NPC247195
0.8072	Intermediate Similarity	NPC12933
0.8072	Intermediate Similarity	NPC50658
0.8068	Intermediate Similarity	NPC77756
0.8049	Intermediate Similarity	NPC220379
0.8046	Intermediate Similarity	NPC236459
0.8026	Intermediate Similarity	NPC472984
0.8026	Intermediate Similarity	NPC41542
0.8025	Intermediate Similarity	NPC23884
0.8022	Intermediate Similarity	NPC476318
0.8022	Intermediate Similarity	NPC476327
0.8	Intermediate Similarity	NPC174964
0.8	Intermediate Similarity	NPC97534
0.8	Intermediate Similarity	NPC471044
0.8	Intermediate Similarity	NPC473336
0.8	Intermediate Similarity	NPC230047
0.8	Intermediate Similarity	NPC34984
0.8	Intermediate Similarity	NPC25037
0.8	Intermediate Similarity	NPC19311
0.8	Intermediate Similarity	NPC9060
0.8	Intermediate Similarity	NPC50438
0.8	Intermediate Similarity	NPC195155
0.8	Intermediate Similarity	NPC181871
0.7978	Intermediate Similarity	NPC475708
0.7935	Intermediate Similarity	NPC189880
0.7922	Intermediate Similarity	NPC469987
0.7922	Intermediate Similarity	NPC475977
0.7907	Intermediate Similarity	NPC474572
0.7907	Intermediate Similarity	NPC477205
0.7901	Intermediate Similarity	NPC472486
0.7901	Intermediate Similarity	NPC472487
0.7895	Intermediate Similarity	NPC225238
0.7875	Intermediate Similarity	NPC74639
0.7857	Intermediate Similarity	NPC58631
0.7857	Intermediate Similarity	NPC73515
0.7849	Intermediate Similarity	NPC58942
0.7849	Intermediate Similarity	NPC475876
0.7849	Intermediate Similarity	NPC260149
0.7848	Intermediate Similarity	NPC290058
0.7841	Intermediate Similarity	NPC476435
0.7841	Intermediate Similarity	NPC476379
0.7841	Intermediate Similarity	NPC52169
0.7841	Intermediate Similarity	NPC182797
0.7826	Intermediate Similarity	NPC317573
0.7816	Intermediate Similarity	NPC72638
0.7816	Intermediate Similarity	NPC476726
0.7816	Intermediate Similarity	NPC2783
0.7816	Intermediate Similarity	NPC476727
0.7816	Intermediate Similarity	NPC80700
0.7816	Intermediate Similarity	NPC120395
0.7812	Intermediate Similarity	NPC327093
0.7802	Intermediate Similarity	NPC474529
0.7802	Intermediate Similarity	NPC159365
0.7791	Intermediate Similarity	NPC171789
0.7778	Intermediate Similarity	NPC21220
0.7778	Intermediate Similarity	NPC125767
0.7778	Intermediate Similarity	NPC52756
0.7778	Intermediate Similarity	NPC475878
0.7778	Intermediate Similarity	NPC179858
0.7753	Intermediate Similarity	NPC61543
0.7753	Intermediate Similarity	NPC477443
0.7753	Intermediate Similarity	NPC64872
0.7753	Intermediate Similarity	NPC274330
0.7753	Intermediate Similarity	NPC270768
0.7753	Intermediate Similarity	NPC143232
0.7753	Intermediate Similarity	NPC234346
0.7753	Intermediate Similarity	NPC25906
0.7753	Intermediate Similarity	NPC290972
0.7753	Intermediate Similarity	NPC59263
0.7753	Intermediate Similarity	NPC293048
0.7753	Intermediate Similarity	NPC225585
0.7753	Intermediate Similarity	NPC198664
0.7753	Intermediate Similarity	NPC130520
0.7753	Intermediate Similarity	NPC127689
0.7753	Intermediate Similarity	NPC263393
0.7753	Intermediate Similarity	NPC477440
0.7753	Intermediate Similarity	NPC121798
0.775	Intermediate Similarity	NPC232112
0.775	Intermediate Similarity	NPC475230
0.7742	Intermediate Similarity	NPC470425
0.7738	Intermediate Similarity	NPC125366
0.7733	Intermediate Similarity	NPC290791
0.7733	Intermediate Similarity	NPC292419
0.7727	Intermediate Similarity	NPC307426
0.7727	Intermediate Similarity	NPC252714
0.7727	Intermediate Similarity	NPC68160
0.7727	Intermediate Similarity	NPC264005
0.7727	Intermediate Similarity	NPC130577
0.7727	Intermediate Similarity	NPC98442
0.7727	Intermediate Similarity	NPC242468
0.7727	Intermediate Similarity	NPC269360
0.7727	Intermediate Similarity	NPC102683
0.7727	Intermediate Similarity	NPC51700
0.7727	Intermediate Similarity	NPC263802
0.7727	Intermediate Similarity	NPC171203
0.7727	Intermediate Similarity	NPC142415
0.7727	Intermediate Similarity	NPC33768
0.7727	Intermediate Similarity	NPC88716
0.7727	Intermediate Similarity	NPC293564
0.7727	Intermediate Similarity	NPC18064
0.7722	Intermediate Similarity	NPC192192
0.7717	Intermediate Similarity	NPC139570
0.7717	Intermediate Similarity	NPC474727
0.7711	Intermediate Similarity	NPC329117
0.7701	Intermediate Similarity	NPC477445
0.7701	Intermediate Similarity	NPC264317
0.7701	Intermediate Similarity	NPC294438

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 NPC476071 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	542
0.1-0.2	3643
0.2-0.3	3295
0.3-0.4	1067
0.4-0.5	291
0.5-0.6	242
0.6-0.7	51
0.7-0.8	15
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8608	High Similarity	NPD6115	Approved
0.8608	High Similarity	NPD6114	Approved
0.8608	High Similarity	NPD6697	Approved
0.8608	High Similarity	NPD6118	Approved
0.8354	Intermediate Similarity	NPD6117	Approved
0.825	Intermediate Similarity	NPD6116	Phase 1
0.8228	Intermediate Similarity	NPD3703	Phase 2
0.8101	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7515	Phase 2
0.7284	Intermediate Similarity	NPD4245	Approved
0.7284	Intermediate Similarity	NPD4244	Approved
0.725	Intermediate Similarity	NPD5360	Phase 3
0.725	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7748	Approved
0.7215	Intermediate Similarity	NPD4224	Phase 2
0.7204	Intermediate Similarity	NPD8035	Phase 2
0.7204	Intermediate Similarity	NPD8034	Phase 2
0.7195	Intermediate Similarity	NPD6081	Approved
0.716	Intermediate Similarity	NPD3698	Phase 2
0.7143	Intermediate Similarity	NPD3702	Approved
0.7073	Intermediate Similarity	NPD4789	Approved
0.701	Intermediate Similarity	NPD7902	Approved
0.6988	Remote Similarity	NPD5777	Approved
0.6951	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3671	Phase 1
0.6875	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD8418	Phase 2
0.6786	Remote Similarity	NPD4758	Discontinued
0.6765	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5364	Discontinued
0.6701	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7900	Approved
0.6697	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5328	Approved
0.66	Remote Similarity	NPD7638	Approved
0.6543	Remote Similarity	NPD7909	Approved
0.6538	Remote Similarity	NPD6402	Approved
0.6538	Remote Similarity	NPD7128	Approved
0.6538	Remote Similarity	NPD5739	Approved
0.6538	Remote Similarity	NPD6675	Approved
0.6535	Remote Similarity	NPD7640	Approved
0.6535	Remote Similarity	NPD7639	Approved
0.6509	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6079	Approved
0.6471	Remote Similarity	NPD4787	Phase 1
0.6444	Remote Similarity	NPD7645	Phase 2
0.6422	Remote Similarity	NPD8133	Approved
0.6415	Remote Similarity	NPD6899	Approved
0.6415	Remote Similarity	NPD6881	Approved
0.6415	Remote Similarity	NPD7320	Approved
0.6408	Remote Similarity	NPD7632	Discontinued
0.6374	Remote Similarity	NPD6928	Phase 2
0.6355	Remote Similarity	NPD6373	Approved
0.6355	Remote Similarity	NPD6372	Approved
0.6348	Remote Similarity	NPD8328	Phase 3
0.6344	Remote Similarity	NPD4788	Approved
0.6337	Remote Similarity	NPD4755	Approved
0.6321	Remote Similarity	NPD5697	Approved
0.6321	Remote Similarity	NPD5701	Approved
0.6316	Remote Similarity	NPD3618	Phase 1
0.6304	Remote Similarity	NPD1779	Approved
0.6304	Remote Similarity	NPD1780	Approved
0.6296	Remote Similarity	NPD7290	Approved
0.6296	Remote Similarity	NPD6883	Approved
0.6296	Remote Similarity	NPD7102	Approved
0.6289	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD4786	Approved
0.6273	Remote Similarity	NPD4632	Approved
0.6263	Remote Similarity	NPD6399	Phase 3
0.6262	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD3198	Approved
0.625	Remote Similarity	NPD3573	Approved
0.6239	Remote Similarity	NPD6847	Approved
0.6239	Remote Similarity	NPD6617	Approved
0.6239	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD8130	Phase 1
0.6239	Remote Similarity	NPD6650	Approved
0.6239	Remote Similarity	NPD6649	Approved
0.6239	Remote Similarity	NPD6869	Approved
0.6238	Remote Similarity	NPD5222	Approved
0.6238	Remote Similarity	NPD5221	Approved
0.6238	Remote Similarity	NPD4697	Phase 3
0.6238	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD3667	Approved
0.6214	Remote Similarity	NPD4700	Approved
0.6214	Remote Similarity	NPD5286	Approved
0.6214	Remote Similarity	NPD4696	Approved
0.6214	Remote Similarity	NPD5285	Approved
0.6204	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6014	Approved
0.6204	Remote Similarity	NPD6013	Approved
0.6204	Remote Similarity	NPD6012	Approved
0.6196	Remote Similarity	NPD7525	Registered
0.6182	Remote Similarity	NPD8297	Approved
0.6182	Remote Similarity	NPD6882	Approved
0.6176	Remote Similarity	NPD5173	Approved
0.617	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.617	Remote Similarity	NPD3669	Approved
0.6162	Remote Similarity	NPD6411	Approved
0.6154	Remote Similarity	NPD5223	Approved
0.6154	Remote Similarity	NPD1700	Approved
0.6126	Remote Similarity	NPD8298	Phase 2
0.6106	Remote Similarity	NPD6009	Approved
0.6102	Remote Similarity	NPD7507	Approved
0.61	Remote Similarity	NPD4202	Approved
0.6095	Remote Similarity	NPD5226	Approved
0.6095	Remote Similarity	NPD5225	Approved
0.6095	Remote Similarity	NPD4633	Approved
0.6095	Remote Similarity	NPD5224	Approved
0.6095	Remote Similarity	NPD5211	Phase 2
0.6078	Remote Similarity	NPD7614	Phase 1
0.6075	Remote Similarity	NPD6008	Approved
0.6038	Remote Similarity	NPD5174	Approved
0.6038	Remote Similarity	NPD5175	Approved
0.6038	Remote Similarity	NPD4754	Approved
0.6034	Remote Similarity	NPD6921	Approved
0.6026	Remote Similarity	NPD615	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6083	Phase 2
0.6019	Remote Similarity	NPD6084	Phase 2
0.6018	Remote Similarity	NPD6940	Discontinued
0.6	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD7736	Approved
0.6	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD5141	Approved
0.596	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.596	Remote Similarity	NPD6101	Approved
0.595	Remote Similarity	NPD7319	Approved
0.5948	Remote Similarity	NPD6319	Approved
0.5941	Remote Similarity	NPD5778	Approved
0.5941	Remote Similarity	NPD5779	Approved
0.5941	Remote Similarity	NPD8171	Discontinued
0.5938	Remote Similarity	NPD3133	Approved
0.5938	Remote Similarity	NPD3665	Phase 1
0.5938	Remote Similarity	NPD3666	Approved
0.5932	Remote Similarity	NPD7604	Phase 2
0.5926	Remote Similarity	NPD6920	Discontinued
0.5926	Remote Similarity	NPD4768	Approved
0.5926	Remote Similarity	NPD4767	Approved
0.5913	Remote Similarity	NPD6335	Approved
0.5897	Remote Similarity	NPD5983	Phase 2
0.5882	Remote Similarity	NPD7492	Approved
0.5877	Remote Similarity	NPD6868	Approved
0.5877	Remote Similarity	NPD6274	Approved
0.5862	Remote Similarity	NPD7101	Approved
0.5862	Remote Similarity	NPD7100	Approved
0.5833	Remote Similarity	NPD6336	Discontinued
0.5833	Remote Similarity	NPD6616	Approved
0.5826	Remote Similarity	NPD6317	Approved
0.5826	Remote Similarity	NPD7115	Discovery
0.5818	Remote Similarity	NPD4730	Approved
0.5818	Remote Similarity	NPD4729	Approved
0.5818	Remote Similarity	NPD5128	Approved
0.5816	Remote Similarity	NPD6684	Approved
0.5816	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD7334	Approved
0.5816	Remote Similarity	NPD7146	Approved
0.5816	Remote Similarity	NPD5330	Approved
0.5816	Remote Similarity	NPD7521	Approved
0.5816	Remote Similarity	NPD6409	Approved
0.5812	Remote Similarity	NPD6059	Approved
0.5812	Remote Similarity	NPD6054	Approved
0.5806	Remote Similarity	NPD4802	Phase 2
0.5806	Remote Similarity	NPD4238	Approved
0.58	Remote Similarity	NPD4753	Phase 2
0.5785	Remote Similarity	NPD7078	Approved
0.5785	Remote Similarity	NPD8293	Discontinued
0.5776	Remote Similarity	NPD6313	Approved
0.5776	Remote Similarity	NPD6314	Approved
0.5773	Remote Similarity	NPD3668	Phase 3
0.5769	Remote Similarity	NPD7732	Phase 3
0.5765	Remote Similarity	NPD371	Approved
0.5763	Remote Similarity	NPD6908	Approved
0.5763	Remote Similarity	NPD6909	Approved
0.5743	Remote Similarity	NPD6700	Approved
0.5743	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5733	Remote Similarity	NPD384	Approved
0.5733	Remote Similarity	NPD385	Approved
0.5727	Remote Similarity	NPD6412	Phase 2
0.5727	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5247	Approved
0.5714	Remote Similarity	NPD5135	Approved
0.5714	Remote Similarity	NPD5250	Approved
0.5714	Remote Similarity	NPD5249	Phase 3
0.5714	Remote Similarity	NPD5251	Approved
0.5714	Remote Similarity	NPD5248	Approved
0.5714	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6370	Approved
0.5714	Remote Similarity	NPD1810	Approved
0.5714	Remote Similarity	NPD1811	Approved
0.5714	Remote Similarity	NPD5169	Approved
0.57	Remote Similarity	NPD5737	Approved
0.57	Remote Similarity	NPD6672	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data