NPASS Compound

Structure

NPC470078 OpenBabel07101718232D 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 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 -0.9000 -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 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 -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 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 1 20 2 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 7 29 1 0 0 0 0 9 10 2 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 24 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 23 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 17 28 1 0 0 0 0 18 30 1 0 0 0 0 19 29 1 0 0 0 0 21 3 1 6 0 0 0 21 22 1 0 0 0 0 22 29 1 6 0 0 0 23 24 1 0 0 0 0 23 28 1 1 0 0 0 24 30 1 0 0 0 0 25 27 1 0 0 0 0 25 28 1 0 0 0 0 26 27 1 0 0 0 0 26 31 2 0 0 0 0 28 6 1 1 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.35
Volume:	491.455
LogP:	7.117
LogD:	5.392
LogS:	-6.059
# Rotatable Bonds:	4
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.329
Synthetic Accessibility Score:	4.759
Fsp3:	0.767
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:	-4.861
MDCK Permeability:	7.699257366766687e-06
Pgp-inhibitor:	0.225
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.052
30% Bioavailability (F30%):	0.781

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.203
Plasma Protein Binding (PPB):	97.65679931640625%
Volume Distribution (VD):	1.223
Pgp-substrate:	1.9597183465957642%

ADMET: Metabolism

CYP1A2-inhibitor:	0.152
CYP1A2-substrate:	0.703
CYP2C19-inhibitor:	0.455
CYP2C19-substrate:	0.95
CYP2C9-inhibitor:	0.586
CYP2C9-substrate:	0.804
CYP2D6-inhibitor:	0.645
CYP2D6-substrate:	0.595
CYP3A4-inhibitor:	0.952
CYP3A4-substrate:	0.876

ADMET: Excretion

Clearance (CL):	9.754
Half-life (T1/2):	0.048

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.323
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.495
Maximum Recommended Daily Dose:	0.877
Skin Sensitization:	0.523
Carcinogencity:	0.45
Eye Corrosion:	0.232
Eye Irritation:	0.193
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC470078

Natural Product ID:	NPC470078
*Common Name:**	Cornusalterin D
IUPAC Name:	(9R,10R,13S,14S,17S)-4,4,10,13,14-pentamethyl-17-[(2S,4E)-6-methylhepta-4,6-dien-2-yl]-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Synonyms:	Cornusalterin D
Standard InCHIKey:	SPMYJZJNYRWSFW-ICRZDDGFSA-N
Standard InCHI:	InChI=1S/C30H46O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h9-10,12,21-23,25H,1,11,13-19H2,2-8H3/b10-9+/t21-,22-,23-,25?,28+,29-,30+/m0/s1
SMILES:	CC(=C)/C=C/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
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669592
PubChem CID:	53318193
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	=	26900.0	nM	PMID[448433]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	14530.0	nM	PMID[448433]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	12730.0	nM	PMID[448433]
NPT574	Cell Line	XF498	Homo sapiens	IC50	=	17760.0	nM	PMID[448433]

☑ 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 NPC470078 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	193
0.1-0.2	1760
0.2-0.3	11134
0.3-0.4	14460
0.4-0.5	8097
0.5-0.6	4881
0.6-0.7	1740
0.7-0.8	367
0.8-0.85	22
0.85-0.9	27
0.9-0.95	13
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC182815
0.9545	High Similarity	NPC20610
0.9412	High Similarity	NPC115023
0.9275	High Similarity	NPC251705
0.9265	High Similarity	NPC159577
0.9265	High Similarity	NPC35734
0.9265	High Similarity	NPC282593
0.9242	High Similarity	NPC323005
0.913	High Similarity	NPC234707
0.9014	High Similarity	NPC293803
0.9014	High Similarity	NPC473171
0.9	High Similarity	NPC303613
0.9	High Similarity	NPC470045
0.9	High Similarity	NPC474228
0.9	High Similarity	NPC470044
0.8986	High Similarity	NPC214770
0.8986	High Similarity	NPC307176
0.8986	High Similarity	NPC40574
0.8986	High Similarity	NPC477856
0.8939	High Similarity	NPC469662
0.8889	High Similarity	NPC69408
0.8873	High Similarity	NPC309852
0.8873	High Similarity	NPC474796
0.8873	High Similarity	NPC329866
0.8873	High Similarity	NPC474797
0.8857	High Similarity	NPC305501
0.8857	High Similarity	NPC54123
0.8841	High Similarity	NPC139397
0.8788	High Similarity	NPC202118
0.8788	High Similarity	NPC197238
0.8714	High Similarity	NPC265782
0.8714	High Similarity	NPC251929
0.8714	High Similarity	NPC2634
0.8714	High Similarity	NPC260040
0.8649	High Similarity	NPC470052
0.8649	High Similarity	NPC82635
0.8611	High Similarity	NPC255021
0.8592	High Similarity	NPC181204
0.8551	High Similarity	NPC176107
0.8533	High Similarity	NPC170793
0.8514	High Similarity	NPC91665
0.8493	Intermediate Similarity	NPC255650
0.8429	Intermediate Similarity	NPC39157
0.8429	Intermediate Similarity	NPC296697
0.8429	Intermediate Similarity	NPC142754
0.8429	Intermediate Similarity	NPC310992
0.8429	Intermediate Similarity	NPC82477
0.8421	Intermediate Similarity	NPC474509
0.8406	Intermediate Similarity	NPC189917
0.8406	Intermediate Similarity	NPC168824
0.8406	Intermediate Similarity	NPC107704
0.8406	Intermediate Similarity	NPC96812
0.8406	Intermediate Similarity	NPC39462
0.8406	Intermediate Similarity	NPC43300
0.8406	Intermediate Similarity	NPC92327
0.8378	Intermediate Similarity	NPC469793
0.8378	Intermediate Similarity	NPC469796
0.8312	Intermediate Similarity	NPC4166
0.831	Intermediate Similarity	NPC286814
0.8286	Intermediate Similarity	NPC20181
0.8286	Intermediate Similarity	NPC220210
0.8267	Intermediate Similarity	NPC470557
0.8205	Intermediate Similarity	NPC311092
0.8169	Intermediate Similarity	NPC260474
0.8169	Intermediate Similarity	NPC188292
0.8101	Intermediate Similarity	NPC83569
0.8101	Intermediate Similarity	NPC69279
0.8088	Intermediate Similarity	NPC213152
0.8088	Intermediate Similarity	NPC60565
0.8082	Intermediate Similarity	NPC5701
0.8082	Intermediate Similarity	NPC190035
0.8082	Intermediate Similarity	NPC225467
0.8082	Intermediate Similarity	NPC223187
0.8077	Intermediate Similarity	NPC147066
0.8056	Intermediate Similarity	NPC477857
0.8056	Intermediate Similarity	NPC256846
0.8052	Intermediate Similarity	NPC215843
0.8052	Intermediate Similarity	NPC90965
0.803	Intermediate Similarity	NPC267626
0.803	Intermediate Similarity	NPC230823
0.803	Intermediate Similarity	NPC49575
0.803	Intermediate Similarity	NPC55004
0.8028	Intermediate Similarity	NPC193770
0.8	Intermediate Similarity	NPC87552
0.8	Intermediate Similarity	NPC268039
0.7975	Intermediate Similarity	NPC469805
0.7975	Intermediate Similarity	NPC469804
0.7975	Intermediate Similarity	NPC320514
0.7975	Intermediate Similarity	NPC472239
0.7973	Intermediate Similarity	NPC474488
0.7971	Intermediate Similarity	NPC165695
0.7941	Intermediate Similarity	NPC127582
0.7927	Intermediate Similarity	NPC476293
0.7922	Intermediate Similarity	NPC469996
0.7917	Intermediate Similarity	NPC87141
0.791	Intermediate Similarity	NPC469769
0.7901	Intermediate Similarity	NPC29447
0.7901	Intermediate Similarity	NPC470048
0.7895	Intermediate Similarity	NPC474463
0.7887	Intermediate Similarity	NPC176171
0.7875	Intermediate Similarity	NPC470046
0.7875	Intermediate Similarity	NPC279639
0.7875	Intermediate Similarity	NPC470047
0.7875	Intermediate Similarity	NPC474790
0.7875	Intermediate Similarity	NPC3856
0.7875	Intermediate Similarity	NPC474976
0.7875	Intermediate Similarity	NPC21667
0.7857	Intermediate Similarity	NPC475124
0.7857	Intermediate Similarity	NPC212210
0.7857	Intermediate Similarity	NPC285371
0.7848	Intermediate Similarity	NPC38350
0.7848	Intermediate Similarity	NPC201912
0.7831	Intermediate Similarity	NPC472220
0.7831	Intermediate Similarity	NPC97884
0.7821	Intermediate Similarity	NPC477371
0.7805	Intermediate Similarity	NPC473168
0.7794	Intermediate Similarity	NPC472304
0.7794	Intermediate Similarity	NPC276764
0.7778	Intermediate Similarity	NPC82902
0.7778	Intermediate Similarity	NPC214043
0.7778	Intermediate Similarity	NPC59453
0.7778	Intermediate Similarity	NPC221758
0.7778	Intermediate Similarity	NPC85774
0.775	Intermediate Similarity	NPC193347
0.775	Intermediate Similarity	NPC260956
0.775	Intermediate Similarity	NPC3511
0.775	Intermediate Similarity	NPC142253
0.775	Intermediate Similarity	NPC100297
0.775	Intermediate Similarity	NPC469806
0.775	Intermediate Similarity	NPC469799
0.775	Intermediate Similarity	NPC472867
0.7746	Intermediate Similarity	NPC251118
0.7727	Intermediate Similarity	NPC200258
0.7722	Intermediate Similarity	NPC472478
0.7722	Intermediate Similarity	NPC469798
0.7722	Intermediate Similarity	NPC469797
0.7714	Intermediate Similarity	NPC472306
0.7711	Intermediate Similarity	NPC93778
0.7711	Intermediate Similarity	NPC163016
0.7711	Intermediate Similarity	NPC136548
0.7711	Intermediate Similarity	NPC75315
0.7711	Intermediate Similarity	NPC58063
0.7683	Intermediate Similarity	NPC474218
0.7683	Intermediate Similarity	NPC471224
0.7683	Intermediate Similarity	NPC470223
0.7683	Intermediate Similarity	NPC469948
0.7681	Intermediate Similarity	NPC25853
0.7654	Intermediate Similarity	NPC41539
0.7647	Intermediate Similarity	NPC30215
0.7647	Intermediate Similarity	NPC266295
0.7647	Intermediate Similarity	NPC27610
0.7647	Intermediate Similarity	NPC94991
0.7647	Intermediate Similarity	NPC56905
0.7632	Intermediate Similarity	NPC159497
0.7625	Intermediate Similarity	NPC477372
0.7625	Intermediate Similarity	NPC474955
0.7606	Intermediate Similarity	NPC4638
0.7595	Intermediate Similarity	NPC190211
0.7595	Intermediate Similarity	NPC474113
0.759	Intermediate Similarity	NPC89077
0.759	Intermediate Similarity	NPC470051
0.759	Intermediate Similarity	NPC474732
0.759	Intermediate Similarity	NPC474778
0.759	Intermediate Similarity	NPC145879
0.759	Intermediate Similarity	NPC222613
0.759	Intermediate Similarity	NPC31564
0.759	Intermediate Similarity	NPC264127
0.759	Intermediate Similarity	NPC474733
0.759	Intermediate Similarity	NPC475022
0.759	Intermediate Similarity	NPC470050
0.759	Intermediate Similarity	NPC51014
0.759	Intermediate Similarity	NPC469994
0.759	Intermediate Similarity	NPC118648
0.7561	Intermediate Similarity	NPC181743
0.7561	Intermediate Similarity	NPC178025
0.7561	Intermediate Similarity	NPC237712
0.7561	Intermediate Similarity	NPC144258
0.7561	Intermediate Similarity	NPC473246
0.7561	Intermediate Similarity	NPC16287
0.7558	Intermediate Similarity	NPC204341
0.7536	Intermediate Similarity	NPC259261
0.7534	Intermediate Similarity	NPC475523
0.7531	Intermediate Similarity	NPC321289
0.7531	Intermediate Similarity	NPC327969
0.7531	Intermediate Similarity	NPC328351
0.7531	Intermediate Similarity	NPC133391
0.7531	Intermediate Similarity	NPC240302
0.7531	Intermediate Similarity	NPC151519
0.7529	Intermediate Similarity	NPC262043
0.7529	Intermediate Similarity	NPC2983
0.7529	Intermediate Similarity	NPC474844
0.75	Intermediate Similarity	NPC141292
0.75	Intermediate Similarity	NPC317590
0.75	Intermediate Similarity	NPC115385
0.75	Intermediate Similarity	NPC136948
0.75	Intermediate Similarity	NPC287063
0.75	Intermediate Similarity	NPC96496
0.75	Intermediate Similarity	NPC90652
0.75	Intermediate Similarity	NPC475740
0.747	Intermediate Similarity	NPC60350

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 NPC470078 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1654
0.2-0.3	4622
0.3-0.4	1913
0.4-0.5	420
0.5-0.6	145
0.6-0.7	135
0.7-0.8	66
0.8-0.85	0
0.85-0.9	3
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9143	High Similarity	NPD4687	Approved
0.9143	High Similarity	NPD4058	Approved
0.9143	High Similarity	NPD5733	Approved
0.8986	High Similarity	NPD4747	Approved
0.8971	High Similarity	NPD3621	Clinical (unspecified phase)
0.8857	High Similarity	NPD5276	Approved
0.8841	High Similarity	NPD4137	Phase 3
0.8714	High Similarity	NPD4691	Approved
0.7875	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4786	Approved
0.775	Intermediate Similarity	NPD4221	Approved
0.775	Intermediate Similarity	NPD4223	Phase 3
0.7683	Intermediate Similarity	NPD5329	Approved
0.759	Intermediate Similarity	NPD5280	Approved
0.759	Intermediate Similarity	NPD6098	Approved
0.759	Intermediate Similarity	NPD4694	Approved
0.7561	Intermediate Similarity	NPD4197	Approved
0.7531	Intermediate Similarity	NPD3667	Approved
0.7442	Intermediate Similarity	NPD5207	Approved
0.7412	Intermediate Similarity	NPD5737	Approved
0.7412	Intermediate Similarity	NPD6672	Approved
0.7381	Intermediate Similarity	NPD6684	Approved
0.7381	Intermediate Similarity	NPD4688	Approved
0.7381	Intermediate Similarity	NPD7334	Approved
0.7381	Intermediate Similarity	NPD5690	Phase 2
0.7381	Intermediate Similarity	NPD4690	Approved
0.7381	Intermediate Similarity	NPD5279	Phase 3
0.7381	Intermediate Similarity	NPD4138	Approved
0.7381	Intermediate Similarity	NPD5205	Approved
0.7381	Intermediate Similarity	NPD4689	Approved
0.7381	Intermediate Similarity	NPD7521	Approved
0.7381	Intermediate Similarity	NPD4693	Phase 3
0.7381	Intermediate Similarity	NPD6409	Approved
0.7381	Intermediate Similarity	NPD5330	Approved
0.7381	Intermediate Similarity	NPD7146	Approved
0.7356	Intermediate Similarity	NPD5281	Approved
0.7356	Intermediate Similarity	NPD5694	Approved
0.7356	Intermediate Similarity	NPD6079	Approved
0.7356	Intermediate Similarity	NPD6050	Approved
0.7356	Intermediate Similarity	NPD5284	Approved
0.7349	Intermediate Similarity	NPD3668	Phase 3
0.7349	Intermediate Similarity	NPD3665	Phase 1
0.7349	Intermediate Similarity	NPD3133	Approved
0.7349	Intermediate Similarity	NPD3666	Approved
0.7326	Intermediate Similarity	NPD6080	Approved
0.7326	Intermediate Similarity	NPD6904	Approved
0.7326	Intermediate Similarity	NPD5328	Approved
0.7326	Intermediate Similarity	NPD6673	Approved
0.725	Intermediate Similarity	NPD3617	Approved
0.7241	Intermediate Similarity	NPD5692	Phase 3
0.7209	Intermediate Similarity	NPD6903	Approved
0.7209	Intermediate Similarity	NPD5208	Approved
0.7209	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4785	Approved
0.7179	Intermediate Similarity	NPD4784	Approved
0.7176	Intermediate Similarity	NPD3618	Phase 1
0.716	Intermediate Similarity	NPD4195	Approved
0.7143	Intermediate Similarity	NPD4243	Approved
0.7143	Intermediate Similarity	NPD287	Approved
0.7126	Intermediate Similarity	NPD4753	Phase 2
0.7079	Intermediate Similarity	NPD6399	Phase 3
0.7045	Intermediate Similarity	NPD4096	Approved
0.7013	Intermediate Similarity	NPD7144	Approved
0.7013	Intermediate Similarity	NPD7143	Approved
0.7011	Intermediate Similarity	NPD4518	Approved
0.6988	Remote Similarity	NPD4692	Approved
0.6988	Remote Similarity	NPD8028	Phase 2
0.6988	Remote Similarity	NPD4139	Approved
0.6977	Remote Similarity	NPD4623	Approved
0.6977	Remote Similarity	NPD4519	Discontinued
0.6977	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5693	Phase 1
0.6923	Remote Similarity	NPD7151	Approved
0.6923	Remote Similarity	NPD7150	Approved
0.6923	Remote Similarity	NPD4629	Approved
0.6923	Remote Similarity	NPD7152	Approved
0.6923	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5210	Approved
0.6889	Remote Similarity	NPD5133	Approved
0.6889	Remote Similarity	NPD4202	Approved
0.6883	Remote Similarity	NPD6923	Approved
0.6883	Remote Similarity	NPD6922	Approved
0.6875	Remote Similarity	NPD6942	Approved
0.6875	Remote Similarity	NPD7339	Approved
0.6867	Remote Similarity	NPD4695	Discontinued
0.6848	Remote Similarity	NPD5221	Approved
0.6848	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5222	Approved
0.6824	Remote Similarity	NPD4788	Approved
0.6813	Remote Similarity	NPD6001	Approved
0.6774	Remote Similarity	NPD6084	Phase 2
0.6774	Remote Similarity	NPD6083	Phase 2
0.6774	Remote Similarity	NPD5173	Approved
0.6742	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5654	Approved
0.6705	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD4190	Phase 3
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD5275	Approved
0.6632	Remote Similarity	NPD4696	Approved
0.6632	Remote Similarity	NPD5286	Approved
0.6632	Remote Similarity	NPD5285	Approved
0.663	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5959	Approved
0.6596	Remote Similarity	NPD4755	Approved
0.6582	Remote Similarity	NPD6939	Phase 2
0.6582	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5223	Approved
0.6559	Remote Similarity	NPD5695	Phase 3
0.6543	Remote Similarity	NPD6926	Approved
0.6543	Remote Similarity	NPD6924	Approved
0.6526	Remote Similarity	NPD5696	Approved
0.6506	Remote Similarity	NPD6932	Approved
0.6495	Remote Similarity	NPD5226	Approved
0.6495	Remote Similarity	NPD4633	Approved
0.6495	Remote Similarity	NPD5224	Approved
0.6495	Remote Similarity	NPD5211	Phase 2
0.6495	Remote Similarity	NPD5225	Approved
0.6495	Remote Similarity	NPD5091	Approved
0.6477	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4700	Approved
0.6458	Remote Similarity	NPD6404	Discontinued
0.6429	Remote Similarity	NPD6052	Approved
0.6429	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7145	Approved
0.6429	Remote Similarity	NPD5174	Approved
0.6429	Remote Similarity	NPD5175	Approved
0.6421	Remote Similarity	NPD3495	Discontinued
0.6413	Remote Similarity	NPD7515	Phase 2
0.64	Remote Similarity	NPD6614	Approved
0.6386	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD6933	Approved
0.6364	Remote Similarity	NPD5141	Approved
0.6337	Remote Similarity	NPD6881	Approved
0.6337	Remote Similarity	NPD6899	Approved
0.6329	Remote Similarity	NPD5360	Phase 3
0.6329	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD8262	Approved
0.631	Remote Similarity	NPD6925	Approved
0.631	Remote Similarity	NPD5776	Phase 2
0.63	Remote Similarity	NPD5739	Approved
0.63	Remote Similarity	NPD6402	Approved
0.63	Remote Similarity	NPD7128	Approved
0.63	Remote Similarity	NPD6675	Approved
0.6279	Remote Similarity	NPD7525	Registered
0.6279	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD7514	Phase 3
0.6277	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7748	Approved
0.6277	Remote Similarity	NPD7900	Approved
0.6265	Remote Similarity	NPD8039	Approved
0.6263	Remote Similarity	NPD4754	Approved
0.6238	Remote Similarity	NPD5697	Approved
0.6237	Remote Similarity	NPD7637	Suspended
0.6235	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7290	Approved
0.6214	Remote Similarity	NPD6883	Approved
0.6214	Remote Similarity	NPD7102	Approved
0.6207	Remote Similarity	NPD6902	Approved
0.6196	Remote Similarity	NPD6051	Approved
0.619	Remote Similarity	NPD7094	Approved
0.619	Remote Similarity	NPD6858	Approved
0.6176	Remote Similarity	NPD4730	Approved
0.6176	Remote Similarity	NPD5168	Approved
0.6176	Remote Similarity	NPD6011	Approved
0.6176	Remote Similarity	NPD4729	Approved
0.6176	Remote Similarity	NPD7320	Approved
0.6173	Remote Similarity	NPD4789	Approved
0.617	Remote Similarity	NPD7631	Approved
0.6163	Remote Similarity	NPD6929	Approved
0.6163	Remote Similarity	NPD6683	Phase 2
0.6154	Remote Similarity	NPD6650	Approved
0.6154	Remote Similarity	NPD8130	Phase 1
0.6154	Remote Similarity	NPD6869	Approved
0.6154	Remote Similarity	NPD6617	Approved
0.6154	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6649	Approved
0.6154	Remote Similarity	NPD6847	Approved
0.6139	Remote Similarity	NPD4768	Approved
0.6139	Remote Similarity	NPD4767	Approved
0.6139	Remote Similarity	NPD6008	Approved
0.6136	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6372	Approved
0.6117	Remote Similarity	NPD6014	Approved
0.6117	Remote Similarity	NPD6013	Approved
0.6117	Remote Similarity	NPD6373	Approved
0.6117	Remote Similarity	NPD6012	Approved
0.6098	Remote Similarity	NPD6081	Approved
0.6098	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD6882	Approved
0.6095	Remote Similarity	NPD8297	Approved
0.6092	Remote Similarity	NPD7332	Phase 2
0.6092	Remote Similarity	NPD6931	Approved
0.6092	Remote Similarity	NPD6930	Phase 2
0.6082	Remote Similarity	NPD7902	Approved
0.6078	Remote Similarity	NPD6412	Phase 2
0.6078	Remote Similarity	NPD5701	Approved
0.6076	Remote Similarity	NPD4224	Phase 2
0.6076	Remote Similarity	NPD7331	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