NPASS Compound

Structure

NPC470046 OpenBabel07101719252D 33 36 0 0 1 0 0 0 0 0999 V2000 -3.1653 -5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5180 -5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5398 -5.6485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 -4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1871 -5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9000 -3.9543 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 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 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2308 -4.6974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 9 33 1 0 0 0 0 10 11 1 0 0 0 0 10 25 2 0 0 0 0 11 26 1 0 0 0 0 12 16 1 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 14 27 1 0 0 0 0 15 29 1 0 0 0 0 16 31 1 0 0 0 0 17 30 1 0 0 0 0 18 20 2 0 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 21 3 1 6 0 0 0 21 23 1 0 0 0 0 22 18 1 1 0 0 0 22 33 1 0 0 0 0 23 30 1 6 0 0 0 24 25 1 0 0 0 0 24 29 1 1 0 0 0 25 31 1 0 0 0 0 26 28 1 0 0 0 0 26 29 1 0 0 0 0 27 28 1 0 0 0 0 27 32 2 0 0 0 0 29 6 1 1 0 0 0 30 31 1 6 0 0 0 31 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.38
Volume:	520.177
LogP:	7.527
LogD:	5.418
LogS:	-6.033
# Rotatable Bonds:	5
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.392
Synthetic Accessibility Score:	4.895
Fsp3:	0.839
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.82
MDCK Permeability:	1.0565533557382878e-05
Pgp-inhibitor:	0.977
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.089
Plasma Protein Binding (PPB):	96.8012924194336%
Volume Distribution (VD):	1.879
Pgp-substrate:	2.136913776397705%

ADMET: Metabolism

CYP1A2-inhibitor:	0.076
CYP1A2-substrate:	0.632
CYP2C19-inhibitor:	0.141
CYP2C19-substrate:	0.954
CYP2C9-inhibitor:	0.258
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.084
CYP2D6-substrate:	0.063
CYP3A4-inhibitor:	0.899
CYP3A4-substrate:	0.879

ADMET: Excretion

Clearance (CL):	11.474
Half-life (T1/2):	0.034

ADMET: Toxicity

hERG Blockers:	0.284
Human Hepatotoxicity (H-HT):	0.796
Drug-inuced Liver Injury (DILI):	0.102
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.293
Maximum Recommended Daily Dose:	0.873
Skin Sensitization:	0.274
Carcinogencity:	0.076
Eye Corrosion:	0.019
Eye Irritation:	0.041
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC470046

Natural Product ID:	NPC470046
*Common Name:**	Cornusalterin G
IUPAC Name:	(9R,10R,13S,14S,17S)-17-[(2S,4R)-4-methoxy-6-methylhept-5-en-2-yl]-4,4,10,13,14-pentamethyl-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Synonyms:	Cornusalterin G
Standard InCHIKey:	UDSUNACNDRCFFJ-SMLRQZPUSA-N
Standard InCHI:	InChI=1S/C31H50O2/c1-20(2)18-22(33-9)19-21(3)23-12-16-31(8)25-10-11-26-28(4,5)27(32)14-15-29(26,6)24(25)13-17-30(23,31)7/h10,18,21-24,26H,11-17,19H2,1-9H3/t21-,22-,23-,24-,26?,29+,30-,31+/m0/s1
SMILES:	CO[C@H](C[C@@H]([C@@H]1CC[C@]2([C@@]1(C)CC[C@H]1C2=CCC2[C@]1(C)CCC(=O)C2(C)C)C)C)C=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668100
PubChem CID:	53317046
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
NPO19594	Cornus walteri	Species	Cornaceae	Eukaryota	n.a.	stem	n.a.	PMID[21182258]
NPO19594	Cornus walteri	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21182258]
NPO19594	Cornus walteri	Species	Cornaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	29880.0	nM	PMID[507364]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	26930.0	nM	PMID[507364]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	18020.0	nM	PMID[507364]
NPT574	Cell Line	XF498	Homo sapiens	IC50	=	20490.0	nM	PMID[507364]

☑ 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 NPC470046 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	177
0.1-0.2	1198
0.2-0.3	5089
0.3-0.4	15359
0.4-0.5	7553
0.5-0.6	6721
0.6-0.7	4810
0.7-0.8	1612
0.8-0.85	145
0.85-0.9	27
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470047
0.9625	High Similarity	NPC470050
0.9625	High Similarity	NPC470051
0.95	High Similarity	NPC470048
0.9024	High Similarity	NPC471224
0.8861	High Similarity	NPC470052
0.8837	High Similarity	NPC190442
0.8795	High Similarity	NPC474083
0.8736	High Similarity	NPC229976
0.869	High Similarity	NPC469994
0.8675	High Similarity	NPC85774
0.8675	High Similarity	NPC82902
0.8675	High Similarity	NPC221758
0.8675	High Similarity	NPC59453
0.8675	High Similarity	NPC214043
0.8605	High Similarity	NPC309603
0.8605	High Similarity	NPC2983
0.8605	High Similarity	NPC473999
0.8588	High Similarity	NPC317590
0.8571	High Similarity	NPC470223
0.8571	High Similarity	NPC474218
0.8571	High Similarity	NPC137493
0.8556	High Similarity	NPC151488
0.8506	High Similarity	NPC320026
0.8506	High Similarity	NPC48010
0.85	High Similarity	NPC470557
0.8488	Intermediate Similarity	NPC28227
0.8471	Intermediate Similarity	NPC51014
0.8471	Intermediate Similarity	NPC195640
0.8471	Intermediate Similarity	NPC474732
0.8471	Intermediate Similarity	NPC474778
0.8471	Intermediate Similarity	NPC145879
0.8471	Intermediate Similarity	NPC474733
0.8471	Intermediate Similarity	NPC264127
0.8471	Intermediate Similarity	NPC31564
0.8452	Intermediate Similarity	NPC473246
0.8444	Intermediate Similarity	NPC78473
0.8434	Intermediate Similarity	NPC328351
0.8434	Intermediate Similarity	NPC151519
0.8409	Intermediate Similarity	NPC475806
0.8409	Intermediate Similarity	NPC473998
0.8395	Intermediate Similarity	NPC469996
0.8391	Intermediate Similarity	NPC177141
0.8372	Intermediate Similarity	NPC58063
0.8372	Intermediate Similarity	NPC90652
0.8372	Intermediate Similarity	NPC475740
0.8353	Intermediate Similarity	NPC323765
0.8353	Intermediate Similarity	NPC469948
0.8352	Intermediate Similarity	NPC126815
0.8352	Intermediate Similarity	NPC291634
0.8333	Intermediate Similarity	NPC33473
0.8315	Intermediate Similarity	NPC474736
0.8313	Intermediate Similarity	NPC474752
0.8313	Intermediate Similarity	NPC147066
0.8313	Intermediate Similarity	NPC82986
0.8313	Intermediate Similarity	NPC7505
0.8313	Intermediate Similarity	NPC474683
0.8313	Intermediate Similarity	NPC474759
0.8313	Intermediate Similarity	NPC474731
0.8295	Intermediate Similarity	NPC273199
0.8295	Intermediate Similarity	NPC198818
0.8295	Intermediate Similarity	NPC69622
0.8293	Intermediate Similarity	NPC215843
0.828	Intermediate Similarity	NPC310981
0.8276	Intermediate Similarity	NPC472220
0.8276	Intermediate Similarity	NPC97884
0.8276	Intermediate Similarity	NPC328313
0.8276	Intermediate Similarity	NPC470417
0.8256	Intermediate Similarity	NPC155011
0.8256	Intermediate Similarity	NPC473168
0.8242	Intermediate Similarity	NPC322063
0.8242	Intermediate Similarity	NPC160056
0.8235	Intermediate Similarity	NPC25833
0.8235	Intermediate Similarity	NPC165064
0.8235	Intermediate Similarity	NPC329043
0.8235	Intermediate Similarity	NPC100391
0.8235	Intermediate Similarity	NPC237712
0.8235	Intermediate Similarity	NPC227064
0.8235	Intermediate Similarity	NPC58841
0.8235	Intermediate Similarity	NPC321187
0.8235	Intermediate Similarity	NPC161423
0.8222	Intermediate Similarity	NPC8993
0.8214	Intermediate Similarity	NPC240302
0.8214	Intermediate Similarity	NPC470049
0.8214	Intermediate Similarity	NPC163236
0.8214	Intermediate Similarity	NPC100297
0.8202	Intermediate Similarity	NPC154101
0.8202	Intermediate Similarity	NPC218301
0.8202	Intermediate Similarity	NPC262870
0.8193	Intermediate Similarity	NPC472478
0.8191	Intermediate Similarity	NPC185530
0.8182	Intermediate Similarity	NPC26959
0.8182	Intermediate Similarity	NPC76879
0.8182	Intermediate Similarity	NPC477943
0.8182	Intermediate Similarity	NPC474245
0.8182	Intermediate Similarity	NPC268406
0.8182	Intermediate Similarity	NPC186688
0.8182	Intermediate Similarity	NPC474570
0.8182	Intermediate Similarity	NPC32830
0.8182	Intermediate Similarity	NPC20610
0.8182	Intermediate Similarity	NPC1015
0.8182	Intermediate Similarity	NPC31985
0.8171	Intermediate Similarity	NPC82635
0.8161	Intermediate Similarity	NPC93778
0.8161	Intermediate Similarity	NPC142361
0.8161	Intermediate Similarity	NPC96496
0.8161	Intermediate Similarity	NPC474684
0.8152	Intermediate Similarity	NPC57416
0.8152	Intermediate Similarity	NPC475894
0.8152	Intermediate Similarity	NPC107243
0.8152	Intermediate Similarity	NPC253826
0.814	Intermediate Similarity	NPC470574
0.814	Intermediate Similarity	NPC274724
0.814	Intermediate Similarity	NPC189311
0.8132	Intermediate Similarity	NPC271195
0.8118	Intermediate Similarity	NPC193198
0.8118	Intermediate Similarity	NPC476082
0.8118	Intermediate Similarity	NPC170862
0.8118	Intermediate Similarity	NPC278648
0.8111	Intermediate Similarity	NPC472930
0.8111	Intermediate Similarity	NPC472942
0.8111	Intermediate Similarity	NPC69454
0.8111	Intermediate Similarity	NPC169343
0.8105	Intermediate Similarity	NPC26478
0.8095	Intermediate Similarity	NPC201912
0.8095	Intermediate Similarity	NPC38350
0.809	Intermediate Similarity	NPC171441
0.809	Intermediate Similarity	NPC471896
0.809	Intermediate Similarity	NPC8062
0.8085	Intermediate Similarity	NPC474327
0.8077	Intermediate Similarity	NPC182815
0.8072	Intermediate Similarity	NPC44083
0.8072	Intermediate Similarity	NPC476177
0.8072	Intermediate Similarity	NPC153987
0.8072	Intermediate Similarity	NPC477371
0.8068	Intermediate Similarity	NPC328539
0.8068	Intermediate Similarity	NPC53911
0.8068	Intermediate Similarity	NPC24816
0.8068	Intermediate Similarity	NPC193360
0.8068	Intermediate Similarity	NPC471722
0.8065	Intermediate Similarity	NPC176845
0.8065	Intermediate Similarity	NPC98868
0.8049	Intermediate Similarity	NPC472300
0.8046	Intermediate Similarity	NPC118648
0.8046	Intermediate Similarity	NPC327115
0.8046	Intermediate Similarity	NPC94755
0.8046	Intermediate Similarity	NPC220478
0.8046	Intermediate Similarity	NPC89077
0.8046	Intermediate Similarity	NPC475022
0.8046	Intermediate Similarity	NPC222613
0.8046	Intermediate Similarity	NPC470955
0.8046	Intermediate Similarity	NPC72133
0.8046	Intermediate Similarity	NPC20688
0.8046	Intermediate Similarity	NPC322159
0.8023	Intermediate Similarity	NPC470077
0.8023	Intermediate Similarity	NPC109512
0.8023	Intermediate Similarity	NPC472265
0.8022	Intermediate Similarity	NPC174051
0.8022	Intermediate Similarity	NPC67831
0.8022	Intermediate Similarity	NPC292793
0.8	Intermediate Similarity	NPC320514
0.8	Intermediate Similarity	NPC260956
0.8	Intermediate Similarity	NPC321289
0.8	Intermediate Similarity	NPC303613
0.8	Intermediate Similarity	NPC193347
0.8	Intermediate Similarity	NPC63748
0.8	Intermediate Similarity	NPC477858
0.8	Intermediate Similarity	NPC472975
0.8	Intermediate Similarity	NPC327969
0.8	Intermediate Similarity	NPC474228
0.8	Intermediate Similarity	NPC272746
0.8	Intermediate Similarity	NPC145143
0.8	Intermediate Similarity	NPC233116
0.8	Intermediate Similarity	NPC49420
0.7979	Intermediate Similarity	NPC201406
0.7978	Intermediate Similarity	NPC469323
0.7978	Intermediate Similarity	NPC475921
0.7978	Intermediate Similarity	NPC472970
0.7978	Intermediate Similarity	NPC474704
0.7978	Intermediate Similarity	NPC285982
0.7978	Intermediate Similarity	NPC472971
0.7978	Intermediate Similarity	NPC86319
0.7978	Intermediate Similarity	NPC275740
0.7976	Intermediate Similarity	NPC267517
0.7976	Intermediate Similarity	NPC195424
0.7976	Intermediate Similarity	NPC2482
0.7975	Intermediate Similarity	NPC35734
0.7975	Intermediate Similarity	NPC307176
0.7975	Intermediate Similarity	NPC282593
0.7975	Intermediate Similarity	NPC159577
0.7957	Intermediate Similarity	NPC110937
0.7955	Intermediate Similarity	NPC167877
0.7955	Intermediate Similarity	NPC233836
0.7955	Intermediate Similarity	NPC128644
0.7955	Intermediate Similarity	NPC477228
0.7955	Intermediate Similarity	NPC159046
0.7955	Intermediate Similarity	NPC136548
0.7955	Intermediate Similarity	NPC187376
0.7955	Intermediate Similarity	NPC136948
0.7952	Intermediate Similarity	NPC63020

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 NPC470046 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1390
0.2-0.3	4146
0.3-0.4	2393
0.4-0.5	598
0.5-0.6	161
0.6-0.7	170
0.7-0.8	102
0.8-0.85	19
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8675	High Similarity	NPD4786	Approved
0.8471	Intermediate Similarity	NPD5330	Approved
0.8471	Intermediate Similarity	NPD6409	Approved
0.8471	Intermediate Similarity	NPD7521	Approved
0.8471	Intermediate Similarity	NPD6684	Approved
0.8471	Intermediate Similarity	NPD7334	Approved
0.8471	Intermediate Similarity	NPD7146	Approved
0.8434	Intermediate Similarity	NPD3667	Approved
0.8276	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD6903	Approved
0.8276	Intermediate Similarity	NPD5737	Approved
0.8276	Intermediate Similarity	NPD6672	Approved
0.8235	Intermediate Similarity	NPD3668	Phase 3
0.8235	Intermediate Similarity	NPD3133	Approved
0.8235	Intermediate Similarity	NPD3665	Phase 1
0.8235	Intermediate Similarity	NPD3666	Approved
0.8182	Intermediate Similarity	NPD5328	Approved
0.8111	Intermediate Similarity	NPD6399	Phase 3
0.8046	Intermediate Similarity	NPD3618	Phase 1
0.8046	Intermediate Similarity	NPD6098	Approved
0.8	Intermediate Similarity	NPD6079	Approved
0.8	Intermediate Similarity	NPD4221	Approved
0.8	Intermediate Similarity	NPD4223	Phase 3
0.8	Intermediate Similarity	NPD5693	Phase 1
0.7978	Intermediate Similarity	NPD6051	Approved
0.7975	Intermediate Similarity	NPD4747	Approved
0.7931	Intermediate Similarity	NPD5329	Approved
0.7848	Intermediate Similarity	NPD4137	Phase 3
0.7841	Intermediate Similarity	NPD5279	Phase 3
0.7816	Intermediate Similarity	NPD4197	Approved
0.7791	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6080	Approved
0.7778	Intermediate Similarity	NPD4753	Phase 2
0.7778	Intermediate Similarity	NPD6904	Approved
0.7778	Intermediate Similarity	NPD6673	Approved
0.775	Intermediate Similarity	NPD4691	Approved
0.7722	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD4202	Approved
0.7683	Intermediate Similarity	NPD5733	Approved
0.7667	Intermediate Similarity	NPD5208	Approved
0.764	Intermediate Similarity	NPD4689	Approved
0.764	Intermediate Similarity	NPD4690	Approved
0.764	Intermediate Similarity	NPD4693	Phase 3
0.764	Intermediate Similarity	NPD5205	Approved
0.764	Intermediate Similarity	NPD4688	Approved
0.764	Intermediate Similarity	NPD4138	Approved
0.759	Intermediate Similarity	NPD6942	Approved
0.759	Intermediate Similarity	NPD7339	Approved
0.7579	Intermediate Similarity	NPD6084	Phase 2
0.7579	Intermediate Similarity	NPD6083	Phase 2
0.7553	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3617	Approved
0.7528	Intermediate Similarity	NPD1694	Approved
0.75	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD4788	Approved
0.7474	Intermediate Similarity	NPD5221	Approved
0.7474	Intermediate Similarity	NPD5222	Approved
0.7474	Intermediate Similarity	NPD4697	Phase 3
0.7474	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4687	Approved
0.747	Intermediate Similarity	NPD4058	Approved
0.7444	Intermediate Similarity	NPD5280	Approved
0.7444	Intermediate Similarity	NPD4623	Approved
0.7444	Intermediate Similarity	NPD4694	Approved
0.7444	Intermediate Similarity	NPD4519	Discontinued
0.7444	Intermediate Similarity	NPD5690	Phase 2
0.7439	Intermediate Similarity	NPD5276	Approved
0.7423	Intermediate Similarity	NPD7639	Approved
0.7423	Intermediate Similarity	NPD7640	Approved
0.7419	Intermediate Similarity	NPD6050	Approved
0.7396	Intermediate Similarity	NPD4755	Approved
0.7396	Intermediate Similarity	NPD5173	Approved
0.7368	Intermediate Similarity	NPD4629	Approved
0.7368	Intermediate Similarity	NPD5695	Phase 3
0.7368	Intermediate Similarity	NPD5210	Approved
0.7333	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5696	Approved
0.7312	Intermediate Similarity	NPD5692	Phase 3
0.7312	Intermediate Similarity	NPD5207	Approved
0.7294	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4692	Approved
0.7273	Intermediate Similarity	NPD5211	Phase 2
0.7273	Intermediate Similarity	NPD4139	Approved
0.7263	Intermediate Similarity	NPD7900	Approved
0.7263	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7748	Approved
0.7263	Intermediate Similarity	NPD6001	Approved
0.7253	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD5285	Approved
0.7245	Intermediate Similarity	NPD5286	Approved
0.7245	Intermediate Similarity	NPD4700	Approved
0.7245	Intermediate Similarity	NPD4696	Approved
0.7241	Intermediate Similarity	NPD4195	Approved
0.7234	Intermediate Similarity	NPD7515	Phase 2
0.7234	Intermediate Similarity	NPD5694	Approved
0.7229	Intermediate Similarity	NPD4243	Approved
0.7228	Intermediate Similarity	NPD6402	Approved
0.7228	Intermediate Similarity	NPD5739	Approved
0.7228	Intermediate Similarity	NPD7128	Approved
0.7228	Intermediate Similarity	NPD6675	Approved
0.7196	Intermediate Similarity	NPD7115	Discovery
0.7176	Intermediate Similarity	NPD8039	Approved
0.7172	Intermediate Similarity	NPD5223	Approved
0.7159	Intermediate Similarity	NPD4695	Discontinued
0.7159	Intermediate Similarity	NPD7525	Registered
0.7129	Intermediate Similarity	NPD5141	Approved
0.7126	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5225	Approved
0.71	Intermediate Similarity	NPD4633	Approved
0.71	Intermediate Similarity	NPD5226	Approved
0.71	Intermediate Similarity	NPD5224	Approved
0.7087	Intermediate Similarity	NPD6899	Approved
0.7087	Intermediate Similarity	NPD7320	Approved
0.7087	Intermediate Similarity	NPD6881	Approved
0.7059	Intermediate Similarity	NPD4784	Approved
0.7059	Intermediate Similarity	NPD4785	Approved
0.7059	Intermediate Similarity	NPD6008	Approved
0.7059	Intermediate Similarity	NPD6924	Approved
0.7059	Intermediate Similarity	NPD6926	Approved
0.7053	Intermediate Similarity	NPD5284	Approved
0.7053	Intermediate Similarity	NPD8034	Phase 2
0.7053	Intermediate Similarity	NPD8035	Phase 2
0.7053	Intermediate Similarity	NPD5281	Approved
0.7041	Intermediate Similarity	NPD7902	Approved
0.703	Intermediate Similarity	NPD5174	Approved
0.703	Intermediate Similarity	NPD5175	Approved
0.703	Intermediate Similarity	NPD4754	Approved
0.7024	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5777	Approved
0.7019	Intermediate Similarity	NPD6372	Approved
0.7019	Intermediate Similarity	NPD6373	Approved
0.699	Remote Similarity	NPD6412	Phase 2
0.699	Remote Similarity	NPD5701	Approved
0.699	Remote Similarity	NPD5697	Approved
0.6989	Remote Similarity	NPD3573	Approved
0.6989	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7290	Approved
0.6952	Remote Similarity	NPD6883	Approved
0.6952	Remote Similarity	NPD7102	Approved
0.6947	Remote Similarity	NPD4096	Approved
0.6923	Remote Similarity	NPD6011	Approved
0.6914	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4789	Approved
0.6905	Remote Similarity	NPD4245	Approved
0.6905	Remote Similarity	NPD4244	Approved
0.6897	Remote Similarity	NPD6933	Approved
0.6893	Remote Similarity	NPD4768	Approved
0.6893	Remote Similarity	NPD4767	Approved
0.6887	Remote Similarity	NPD6869	Approved
0.6887	Remote Similarity	NPD8130	Phase 1
0.6887	Remote Similarity	NPD6649	Approved
0.6887	Remote Similarity	NPD6650	Approved
0.6887	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6617	Approved
0.6887	Remote Similarity	NPD6847	Approved
0.6863	Remote Similarity	NPD6052	Approved
0.6857	Remote Similarity	NPD6013	Approved
0.6857	Remote Similarity	NPD6014	Approved
0.6857	Remote Similarity	NPD6012	Approved
0.6854	Remote Similarity	NPD7645	Phase 2
0.6854	Remote Similarity	NPD6929	Approved
0.6837	Remote Similarity	NPD5654	Approved
0.6822	Remote Similarity	NPD8297	Approved
0.6822	Remote Similarity	NPD6882	Approved
0.6804	Remote Similarity	NPD5133	Approved
0.6786	Remote Similarity	NPD3698	Phase 2
0.6786	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6923	Approved
0.6786	Remote Similarity	NPD6922	Approved
0.6786	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5275	Approved
0.6782	Remote Similarity	NPD4190	Phase 3
0.6778	Remote Similarity	NPD6931	Approved
0.6778	Remote Similarity	NPD6930	Phase 2
0.6771	Remote Similarity	NPD5785	Approved
0.6765	Remote Similarity	NPD7632	Discontinued
0.6762	Remote Similarity	NPD4730	Approved
0.6762	Remote Similarity	NPD5168	Approved
0.6762	Remote Similarity	NPD6686	Approved
0.6762	Remote Similarity	NPD4729	Approved
0.6762	Remote Similarity	NPD5128	Approved
0.6739	Remote Similarity	NPD5362	Discontinued
0.6739	Remote Similarity	NPD6695	Phase 3
0.6737	Remote Similarity	NPD4518	Approved
0.6733	Remote Similarity	NPD6404	Discontinued
0.6706	Remote Similarity	NPD7144	Approved
0.6706	Remote Similarity	NPD7143	Approved
0.6701	Remote Similarity	NPD7637	Suspended
0.67	Remote Similarity	NPD5959	Approved
0.6667	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD5360	Phase 3
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6614	Approved
0.6667	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5135	Approved
0.6636	Remote Similarity	NPD5250	Approved
0.6636	Remote Similarity	NPD5248	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