NPASS Compound

Structure

NPC470045 OpenBabel07101719252D 31 34 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 -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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 3.9543 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 -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 -4.3301 -1.5000 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 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 0.9511 1.3090 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 -1.7321 0.0000 0.0000 C 0 0 1 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 -3.4641 0.0000 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 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 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 27 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 23 2 0 0 0 0 13 25 1 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 19 1 0 0 0 0 15 24 1 0 0 0 0 16 17 2 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 29 1 0 0 0 0 19 28 1 0 0 0 0 21 3 1 6 0 0 0 21 22 1 0 0 0 0 22 28 1 6 0 0 0 23 24 1 0 0 0 0 23 29 1 0 0 0 0 24 30 1 1 0 0 0 25 27 1 0 0 0 0 25 30 1 0 0 0 0 26 30 1 0 0 0 0 26 31 2 0 0 0 0 28 29 1 6 0 0 0 29 7 1 1 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.37
Volume:	494.091
LogP:	8.191
LogD:	5.83
LogS:	-6.816
# Rotatable Bonds:	5
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.405
Synthetic Accessibility Score:	4.649
Fsp3:	0.833
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:	-4.77
MDCK Permeability:	1.7185730030178092e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.866
30% Bioavailability (F30%):	0.623

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.189
Plasma Protein Binding (PPB):	97.96688842773438%
Volume Distribution (VD):	1.792
Pgp-substrate:	1.665256381034851%

ADMET: Metabolism

CYP1A2-inhibitor:	0.126
CYP1A2-substrate:	0.207
CYP2C19-inhibitor:	0.391
CYP2C19-substrate:	0.951
CYP2C9-inhibitor:	0.465
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.728
CYP2D6-substrate:	0.023
CYP3A4-inhibitor:	0.947
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	14.976
Half-life (T1/2):	0.004

ADMET: Toxicity

hERG Blockers:	0.821
Human Hepatotoxicity (H-HT):	0.457
Drug-inuced Liver Injury (DILI):	0.069
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.438
Maximum Recommended Daily Dose:	0.845
Skin Sensitization:	0.899
Carcinogencity:	0.761
Eye Corrosion:	0.718
Eye Irritation:	0.159
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC470045

Natural Product ID:	NPC470045
*Common Name:**	Cornusalterin F
IUPAC Name:	(9S,10S,13S,14S,17S)-4,4,10,13,14-pentamethyl-17-[(2S)-6-methylheptan-2-yl]-5,6,9,11,12,15,16,17-octahydrocyclopenta[a]phenanthren-1-one
Synonyms:	Cornusalterin F
Standard InCHIKey:	SRZGQWOHBSWCAT-MHNWUIROSA-N
Standard InCHI:	InChI=1S/C30H48O/c1-20(2)10-9-11-21(3)22-14-18-29(7)23-12-13-25-27(4,5)17-16-26(31)30(25,8)24(23)15-19-28(22,29)6/h12,16-17,20-22,24-25H,9-11,13-15,18-19H2,1-8H3/t21-,22-,24-,25?,28-,29+,30+/m0/s1
SMILES:	CC(CCC[C@@H]([C@@H]1CC[C@]2([C@@]1(C)CC[C@H]1C2=CCC2[C@]1(C)C(=O)C=CC2(C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668099
PubChem CID:	53323673
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	=	27030.0	nM	PMID[496929]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	27280.0	nM	PMID[496929]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	21360.0	nM	PMID[496929]
NPT574	Cell Line	XF498	Homo sapiens	IC50	=	24590.0	nM	PMID[496929]

☑ 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 NPC470045 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	186
0.1-0.2	2083
0.2-0.3	12369
0.3-0.4	13113
0.4-0.5	7952
0.5-0.6	4848
0.6-0.7	1678
0.7-0.8	390
0.8-0.85	39
0.85-0.9	21
0.9-0.95	16
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470044
0.9706	High Similarity	NPC251705
0.9559	High Similarity	NPC234707
0.9559	High Similarity	NPC115023
0.9429	High Similarity	NPC293803
0.942	High Similarity	NPC474228
0.942	High Similarity	NPC303613
0.9412	High Similarity	NPC35734
0.9412	High Similarity	NPC282593
0.9412	High Similarity	NPC159577
0.9296	High Similarity	NPC69408
0.9286	High Similarity	NPC309852
0.9275	High Similarity	NPC54123
0.9275	High Similarity	NPC305501
0.9265	High Similarity	NPC182815
0.913	High Similarity	NPC251929
0.913	High Similarity	NPC265782
0.913	High Similarity	NPC2634
0.913	High Similarity	NPC307176
0.9118	High Similarity	NPC188292
0.9118	High Similarity	NPC20610
0.9118	High Similarity	NPC260474
0.9014	High Similarity	NPC255021
0.9	High Similarity	NPC470078
0.9	High Similarity	NPC5701
0.8986	High Similarity	NPC256846
0.8986	High Similarity	NPC139397
0.8971	High Similarity	NPC176107
0.8919	High Similarity	NPC90965
0.8919	High Similarity	NPC170793
0.8889	High Similarity	NPC255650
0.8857	High Similarity	NPC260040
0.8841	High Similarity	NPC87141
0.8841	High Similarity	NPC310992
0.8824	High Similarity	NPC323005
0.8824	High Similarity	NPC92327
0.88	High Similarity	NPC474509
0.875	High Similarity	NPC474796
0.875	High Similarity	NPC474797
0.875	High Similarity	NPC329866
0.8732	High Similarity	NPC181204
0.8732	High Similarity	NPC223187
0.8676	High Similarity	NPC251118
0.8657	High Similarity	NPC165695
0.863	High Similarity	NPC473171
0.8592	High Similarity	NPC477856
0.8592	High Similarity	NPC214770
0.8592	High Similarity	NPC40574
0.8571	High Similarity	NPC142253
0.8571	High Similarity	NPC3511
0.8551	High Similarity	NPC176171
0.8533	High Similarity	NPC469996
0.8529	High Similarity	NPC212210
0.8529	High Similarity	NPC469662
0.8507	High Similarity	NPC213152
0.8472	Intermediate Similarity	NPC225467
0.8382	Intermediate Similarity	NPC202118
0.8382	Intermediate Similarity	NPC288253
0.8382	Intermediate Similarity	NPC197238
0.8358	Intermediate Similarity	NPC25853
0.8358	Intermediate Similarity	NPC127582
0.8354	Intermediate Similarity	NPC87552
0.8333	Intermediate Similarity	NPC472239
0.8289	Intermediate Similarity	NPC82635
0.8289	Intermediate Similarity	NPC470052
0.8267	Intermediate Similarity	NPC469793
0.8267	Intermediate Similarity	NPC474463
0.8267	Intermediate Similarity	NPC1254
0.8267	Intermediate Similarity	NPC469796
0.8261	Intermediate Similarity	NPC475124
0.8261	Intermediate Similarity	NPC285371
0.825	Intermediate Similarity	NPC8571
0.825	Intermediate Similarity	NPC29447
0.8228	Intermediate Similarity	NPC41539
0.8219	Intermediate Similarity	NPC190035
0.8209	Intermediate Similarity	NPC472304
0.8209	Intermediate Similarity	NPC276764
0.8194	Intermediate Similarity	NPC477857
0.8169	Intermediate Similarity	NPC475523
0.8158	Intermediate Similarity	NPC91665
0.8148	Intermediate Similarity	NPC475022
0.8148	Intermediate Similarity	NPC222613
0.8148	Intermediate Similarity	NPC118648
0.8125	Intermediate Similarity	NPC473246
0.8116	Intermediate Similarity	NPC472306
0.8101	Intermediate Similarity	NPC320514
0.8101	Intermediate Similarity	NPC321289
0.8101	Intermediate Similarity	NPC472867
0.8101	Intermediate Similarity	NPC100297
0.8101	Intermediate Similarity	NPC327969
0.806	Intermediate Similarity	NPC56905
0.806	Intermediate Similarity	NPC266295
0.806	Intermediate Similarity	NPC27610
0.806	Intermediate Similarity	NPC30215
0.806	Intermediate Similarity	NPC94991
0.8056	Intermediate Similarity	NPC142754
0.8056	Intermediate Similarity	NPC39157
0.8056	Intermediate Similarity	NPC155198
0.8056	Intermediate Similarity	NPC296697
0.8056	Intermediate Similarity	NPC82477
0.8052	Intermediate Similarity	NPC228911
0.8049	Intermediate Similarity	NPC93778
0.8028	Intermediate Similarity	NPC168824
0.8028	Intermediate Similarity	NPC189917
0.8028	Intermediate Similarity	NPC43300
0.8028	Intermediate Similarity	NPC107704
0.8028	Intermediate Similarity	NPC39462
0.8028	Intermediate Similarity	NPC96812
0.8025	Intermediate Similarity	NPC472931
0.8025	Intermediate Similarity	NPC472940
0.8025	Intermediate Similarity	NPC11711
0.8	Intermediate Similarity	NPC219232
0.8	Intermediate Similarity	NPC168188
0.8	Intermediate Similarity	NPC128346
0.8	Intermediate Similarity	NPC470015
0.7975	Intermediate Similarity	NPC38350
0.7975	Intermediate Similarity	NPC477372
0.7975	Intermediate Similarity	NPC4166
0.7975	Intermediate Similarity	NPC201912
0.7971	Intermediate Similarity	NPC60565
0.7949	Intermediate Similarity	NPC190211
0.7949	Intermediate Similarity	NPC472490
0.7945	Intermediate Similarity	NPC286814
0.7941	Intermediate Similarity	NPC259261
0.7922	Intermediate Similarity	NPC470557
0.7917	Intermediate Similarity	NPC20181
0.7917	Intermediate Similarity	NPC220210
0.791	Intermediate Similarity	NPC49575
0.791	Intermediate Similarity	NPC55004
0.791	Intermediate Similarity	NPC115385
0.791	Intermediate Similarity	NPC267626
0.791	Intermediate Similarity	NPC230823
0.7901	Intermediate Similarity	NPC178025
0.7901	Intermediate Similarity	NPC214043
0.7901	Intermediate Similarity	NPC320801
0.7901	Intermediate Similarity	NPC181743
0.7901	Intermediate Similarity	NPC85774
0.7901	Intermediate Similarity	NPC16287
0.7895	Intermediate Similarity	NPC476346
0.7882	Intermediate Similarity	NPC204341
0.7875	Intermediate Similarity	NPC469804
0.7875	Intermediate Similarity	NPC193347
0.7875	Intermediate Similarity	NPC469805
0.7875	Intermediate Similarity	NPC260956
0.7875	Intermediate Similarity	NPC311092
0.7857	Intermediate Similarity	NPC262043
0.7857	Intermediate Similarity	NPC32285
0.7848	Intermediate Similarity	NPC472478
0.7831	Intermediate Similarity	NPC58063
0.7831	Intermediate Similarity	NPC136548
0.7831	Intermediate Similarity	NPC476293
0.7826	Intermediate Similarity	NPC270042
0.7821	Intermediate Similarity	NPC115515
0.7821	Intermediate Similarity	NPC105197
0.7821	Intermediate Similarity	NPC189485
0.7805	Intermediate Similarity	NPC469948
0.7805	Intermediate Similarity	NPC60350
0.7805	Intermediate Similarity	NPC94531
0.7805	Intermediate Similarity	NPC311702
0.7805	Intermediate Similarity	NPC123319
0.7794	Intermediate Similarity	NPC311852
0.7794	Intermediate Similarity	NPC60772
0.7778	Intermediate Similarity	NPC474976
0.7778	Intermediate Similarity	NPC279639
0.7778	Intermediate Similarity	NPC83569
0.7778	Intermediate Similarity	NPC3856
0.7778	Intermediate Similarity	NPC474790
0.7778	Intermediate Similarity	NPC69279
0.7765	Intermediate Similarity	NPC191684
0.7763	Intermediate Similarity	NPC211641
0.7763	Intermediate Similarity	NPC159497
0.775	Intermediate Similarity	NPC147066
0.775	Intermediate Similarity	NPC475833
0.7746	Intermediate Similarity	NPC473902
0.7746	Intermediate Similarity	NPC6697
0.7746	Intermediate Similarity	NPC4638
0.7738	Intermediate Similarity	NPC471722
0.7733	Intermediate Similarity	NPC474562
0.7733	Intermediate Similarity	NPC304983
0.7722	Intermediate Similarity	NPC215843
0.7722	Intermediate Similarity	NPC27817
0.7722	Intermediate Similarity	NPC477371
0.7714	Intermediate Similarity	NPC475795
0.7711	Intermediate Similarity	NPC474733
0.7711	Intermediate Similarity	NPC31564
0.7711	Intermediate Similarity	NPC474732
0.7711	Intermediate Similarity	NPC72133
0.7711	Intermediate Similarity	NPC474778
0.7711	Intermediate Similarity	NPC145879
0.7683	Intermediate Similarity	NPC144258
0.7683	Intermediate Similarity	NPC237712
0.7674	Intermediate Similarity	NPC272746
0.7674	Intermediate Similarity	NPC218301
0.7671	Intermediate Similarity	NPC193770
0.7671	Intermediate Similarity	NPC4370
0.7671	Intermediate Similarity	NPC290350
0.7662	Intermediate Similarity	NPC65650
0.7654	Intermediate Similarity	NPC469799
0.7654	Intermediate Similarity	NPC469806
0.7647	Intermediate Similarity	NPC86319

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 NPC470045 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	2199
0.2-0.3	4535
0.3-0.4	1579
0.4-0.5	304
0.5-0.6	173
0.6-0.7	110
0.7-0.8	57
0.8-0.85	3
0.85-0.9	2
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9286	High Similarity	NPD4687	Approved
0.9286	High Similarity	NPD5733	Approved
0.913	High Similarity	NPD4691	Approved
0.913	High Similarity	NPD4747	Approved
0.9014	High Similarity	NPD4058	Approved
0.9	High Similarity	NPD5276	Approved
0.8986	High Similarity	NPD4137	Phase 3
0.8571	High Similarity	NPD3621	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD5690	Phase 2
0.7875	Intermediate Similarity	NPD4223	Phase 3
0.7875	Intermediate Similarity	NPD4221	Approved
0.7805	Intermediate Similarity	NPD5329	Approved
0.7711	Intermediate Similarity	NPD4694	Approved
0.7711	Intermediate Similarity	NPD5280	Approved
0.7683	Intermediate Similarity	NPD4197	Approved
0.7674	Intermediate Similarity	NPD6079	Approved
0.7558	Intermediate Similarity	NPD5207	Approved
0.7536	Intermediate Similarity	NPD287	Approved
0.7531	Intermediate Similarity	NPD8028	Phase 2
0.7529	Intermediate Similarity	NPD5737	Approved
0.7529	Intermediate Similarity	NPD6672	Approved
0.75	Intermediate Similarity	NPD5279	Phase 3
0.75	Intermediate Similarity	NPD4690	Approved
0.75	Intermediate Similarity	NPD4138	Approved
0.75	Intermediate Similarity	NPD4195	Approved
0.75	Intermediate Similarity	NPD6409	Approved
0.75	Intermediate Similarity	NPD4689	Approved
0.75	Intermediate Similarity	NPD4688	Approved
0.75	Intermediate Similarity	NPD7334	Approved
0.75	Intermediate Similarity	NPD5205	Approved
0.75	Intermediate Similarity	NPD6684	Approved
0.75	Intermediate Similarity	NPD4693	Phase 3
0.75	Intermediate Similarity	NPD7146	Approved
0.75	Intermediate Similarity	NPD5330	Approved
0.75	Intermediate Similarity	NPD7521	Approved
0.7471	Intermediate Similarity	NPD5284	Approved
0.7471	Intermediate Similarity	NPD5694	Approved
0.7471	Intermediate Similarity	NPD5281	Approved
0.7471	Intermediate Similarity	NPD6050	Approved
0.747	Intermediate Similarity	NPD3665	Phase 1
0.747	Intermediate Similarity	NPD4786	Approved
0.747	Intermediate Similarity	NPD3666	Approved
0.747	Intermediate Similarity	NPD3133	Approved
0.7442	Intermediate Similarity	NPD6904	Approved
0.7442	Intermediate Similarity	NPD6080	Approved
0.7442	Intermediate Similarity	NPD6673	Approved
0.7442	Intermediate Similarity	NPD5328	Approved
0.7375	Intermediate Similarity	NPD3617	Approved
0.7356	Intermediate Similarity	NPD5692	Phase 3
0.7326	Intermediate Similarity	NPD5208	Approved
0.7326	Intermediate Similarity	NPD6903	Approved
0.7326	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3618	Phase 1
0.7294	Intermediate Similarity	NPD6098	Approved
0.7294	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4753	Phase 2
0.7229	Intermediate Similarity	NPD3667	Approved
0.7222	Intermediate Similarity	NPD5210	Approved
0.7222	Intermediate Similarity	NPD4629	Approved
0.7195	Intermediate Similarity	NPD4695	Discontinued
0.7159	Intermediate Similarity	NPD4096	Approved
0.7143	Intermediate Similarity	NPD5222	Approved
0.7143	Intermediate Similarity	NPD5221	Approved
0.7143	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4518	Approved
0.7108	Intermediate Similarity	NPD4139	Approved
0.7108	Intermediate Similarity	NPD4692	Approved
0.7093	Intermediate Similarity	NPD4519	Discontinued
0.7093	Intermediate Similarity	NPD4623	Approved
0.7079	Intermediate Similarity	NPD5693	Phase 1
0.7065	Intermediate Similarity	NPD5173	Approved
0.7059	Intermediate Similarity	NPD3668	Phase 3
0.7033	Intermediate Similarity	NPD5695	Phase 3
0.7033	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3573	Approved
0.7	Intermediate Similarity	NPD4202	Approved
0.7	Intermediate Similarity	NPD5133	Approved
0.6941	Remote Similarity	NPD4788	Approved
0.6923	Remote Similarity	NPD6001	Approved
0.6915	Remote Similarity	NPD5285	Approved
0.6915	Remote Similarity	NPD5286	Approved
0.6915	Remote Similarity	NPD4696	Approved
0.6882	Remote Similarity	NPD6084	Phase 2
0.6882	Remote Similarity	NPD6083	Phase 2
0.6875	Remote Similarity	NPD4784	Approved
0.6875	Remote Similarity	NPD4785	Approved
0.6848	Remote Similarity	NPD5654	Approved
0.6842	Remote Similarity	NPD5223	Approved
0.6835	Remote Similarity	NPD4243	Approved
0.6813	Remote Similarity	NPD6399	Phase 3
0.6774	Remote Similarity	NPD4697	Phase 3
0.6771	Remote Similarity	NPD4633	Approved
0.6771	Remote Similarity	NPD5225	Approved
0.6771	Remote Similarity	NPD5091	Approved
0.6771	Remote Similarity	NPD5211	Phase 2
0.6771	Remote Similarity	NPD5226	Approved
0.6771	Remote Similarity	NPD5224	Approved
0.6737	Remote Similarity	NPD6404	Discontinued
0.6702	Remote Similarity	NPD5959	Approved
0.6702	Remote Similarity	NPD4755	Approved
0.6701	Remote Similarity	NPD5175	Approved
0.6701	Remote Similarity	NPD5174	Approved
0.6667	Remote Similarity	NPD6614	Approved
0.6667	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5141	Approved
0.6632	Remote Similarity	NPD5696	Approved
0.66	Remote Similarity	NPD6881	Approved
0.66	Remote Similarity	NPD6899	Approved
0.6585	Remote Similarity	NPD7339	Approved
0.6585	Remote Similarity	NPD6942	Approved
0.6562	Remote Similarity	NPD4700	Approved
0.6531	Remote Similarity	NPD6052	Approved
0.6522	Remote Similarity	NPD7515	Phase 2
0.65	Remote Similarity	NPD5697	Approved
0.6471	Remote Similarity	NPD7290	Approved
0.6471	Remote Similarity	NPD7102	Approved
0.6471	Remote Similarity	NPD6883	Approved
0.6437	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD4729	Approved
0.6436	Remote Similarity	NPD5168	Approved
0.6436	Remote Similarity	NPD4730	Approved
0.6436	Remote Similarity	NPD6011	Approved
0.6421	Remote Similarity	NPD7614	Phase 1
0.6421	Remote Similarity	NPD7732	Phase 3
0.641	Remote Similarity	NPD7331	Phase 2
0.6408	Remote Similarity	NPD8130	Phase 1
0.6408	Remote Similarity	NPD6847	Approved
0.6408	Remote Similarity	NPD6649	Approved
0.6408	Remote Similarity	NPD6869	Approved
0.6408	Remote Similarity	NPD6650	Approved
0.6408	Remote Similarity	NPD6617	Approved
0.6404	Remote Similarity	NPD1694	Approved
0.64	Remote Similarity	NPD5739	Approved
0.64	Remote Similarity	NPD6402	Approved
0.64	Remote Similarity	NPD7128	Approved
0.64	Remote Similarity	NPD6675	Approved
0.6395	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD5275	Approved
0.6386	Remote Similarity	NPD4190	Phase 3
0.6383	Remote Similarity	NPD7748	Approved
0.6383	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7900	Approved
0.6373	Remote Similarity	NPD6014	Approved
0.6373	Remote Similarity	NPD6012	Approved
0.6373	Remote Similarity	NPD6013	Approved
0.6364	Remote Similarity	NPD4754	Approved
0.6354	Remote Similarity	NPD3495	Discontinued
0.6353	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD8297	Approved
0.6346	Remote Similarity	NPD6882	Approved
0.6311	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4634	Approved
0.6311	Remote Similarity	NPD5169	Approved
0.6311	Remote Similarity	NPD5251	Approved
0.6311	Remote Similarity	NPD5248	Approved
0.6311	Remote Similarity	NPD5135	Approved
0.6311	Remote Similarity	NPD5250	Approved
0.6311	Remote Similarity	NPD5247	Approved
0.6311	Remote Similarity	NPD5249	Phase 3
0.6296	Remote Similarity	NPD7143	Approved
0.6296	Remote Similarity	NPD7144	Approved
0.6296	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6939	Phase 2
0.6277	Remote Similarity	NPD7631	Approved
0.6275	Remote Similarity	NPD5128	Approved
0.6275	Remote Similarity	NPD7320	Approved
0.625	Remote Similarity	NPD5127	Approved
0.625	Remote Similarity	NPD5215	Approved
0.625	Remote Similarity	NPD5217	Approved
0.625	Remote Similarity	NPD5216	Approved
0.6238	Remote Similarity	NPD4768	Approved
0.6238	Remote Similarity	NPD6008	Approved
0.6238	Remote Similarity	NPD4767	Approved
0.6222	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7151	Approved
0.622	Remote Similarity	NPD7152	Approved
0.622	Remote Similarity	NPD7150	Approved
0.6214	Remote Similarity	NPD6372	Approved
0.6214	Remote Similarity	NPD6373	Approved
0.6186	Remote Similarity	NPD7902	Approved
0.6176	Remote Similarity	NPD5701	Approved
0.6176	Remote Similarity	NPD6412	Phase 2
0.6173	Remote Similarity	NPD6923	Approved
0.6173	Remote Similarity	NPD6922	Approved
0.617	Remote Similarity	NPD7609	Phase 3
0.6168	Remote Similarity	NPD6868	Approved
0.6132	Remote Similarity	NPD4632	Approved
0.6118	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7115	Discovery
0.6095	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD7341	Phase 2
0.6075	Remote Similarity	NPD5167	Approved
0.6055	Remote Similarity	NPD6335	Approved
0.6049	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD5360	Phase 3
0.6023	Remote Similarity	NPD7525	Registered
0.6	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD8262	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