NPASS Compound

Structure

NPC18857 OpenBabel07101719132D 36 39 0 0 1 0 0 0 0 0999 V2000 -4.0313 -5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3840 -6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1042 -2.9680 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 -0.4593 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4570 -3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7660 -4.4543 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4133 -3.9190 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3914 -4.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0531 -5.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 -2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7441 -4.6622 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 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 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0605 -3.3838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4049 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 0.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 8 11 1 0 0 0 0 8 18 1 0 0 0 0 9 12 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 17 1 0 0 0 0 11 27 1 0 0 0 0 12 28 1 0 0 0 0 13 30 1 0 0 0 0 14 19 1 0 0 0 0 14 29 1 0 0 0 0 15 17 1 0 0 0 0 16 3 1 1 0 0 0 16 21 1 0 0 0 0 17 7 1 1 0 0 0 18 23 1 0 0 0 0 18 31 1 1 0 0 0 19 22 1 0 0 0 0 19 32 1 6 0 0 0 20 27 1 1 0 0 0 20 29 1 0 0 0 0 21 24 1 0 0 0 0 21 28 1 1 0 0 0 22 23 1 0 0 0 0 22 27 1 1 0 0 0 23 33 1 1 0 0 0 24 25 1 0 0 0 0 24 34 1 1 0 0 0 25 26 1 0 0 0 0 25 35 1 1 0 0 0 26 28 1 1 0 0 0 26 29 1 0 0 0 0 27 4 1 1 0 0 0 28 5 1 1 0 0 0 29 36 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.37
Volume:	537.446
LogP:	3.172
LogD:	3.453
LogS:	-3.28
# Rotatable Bonds:	7
TPSA:	141.61
# H-Bond Aceptor:	7
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.277
Synthetic Accessibility Score:	5.307
Fsp3:	1.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.091
MDCK Permeability:	4.2565512558212504e-05
Pgp-inhibitor:	0.043
Pgp-substrate:	0.902
Human Intestinal Absorption (HIA):	0.806
20% Bioavailability (F20%):	0.225
30% Bioavailability (F30%):	0.645

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.102
Plasma Protein Binding (PPB):	92.11522674560547%
Volume Distribution (VD):	0.512
Pgp-substrate:	3.1166350841522217%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.778
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.762
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.116
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.1
CYP3A4-substrate:	0.055

ADMET: Excretion

Clearance (CL):	3.07
Half-life (T1/2):	0.39

ADMET: Toxicity

hERG Blockers:	0.233
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.484
Carcinogencity:	0.031
Eye Corrosion:	0.774
Eye Irritation:	0.033
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: NPC18857

Natural Product ID:	NPC18857
*Common Name:**	Certonardosterol P1
IUPAC Name:	(3S,4R,5S,6S,8S,9R,10S,13R,14S,15S,16R,17R)-17-[(2R,5R)-5-(2-hydroxyethyl)-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,4,6,8,15,16-hexol
Synonyms:	Certonardosterol P1
Standard InCHIKey:	LVWCIHZIRLWTAH-CDVCAKAQSA-N
Standard InCHI:	InChI=1S/C29H52O7/c1-15(2)17(10-13-30)7-6-16(3)21-24(34)25(35)26-28(21,5)12-9-20-27(4)11-8-18(31)23(33)22(27)19(32)14-29(20,26)36/h15-26,30-36H,6-14H2,1-5H3/t16-,17-,18+,19+,20-,21+,22+,23+,24-,25-,26-,27-,28-,29+/m1/s1
SMILES:	CC(C)[C@H](CC[C@@H](C)[C@H]1[C@H]([C@H]([C@@H]2[C@]1(C)CC[C@@H]1[C@@]3(C)CC[C@@H]([C@@H]([C@@H]3[C@H](C[C@@]21O)O)O)O)O)O)CCO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464937
PubChem CID:	11409669
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes and derivatives

*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
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444692]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662097]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104487]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497935]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	3.3	ug ml-1	PMID[473136]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	3.5	ug ml-1	PMID[473136]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	2.5	ug ml-1	PMID[473136]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	3.48	ug ml-1	PMID[473136]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	4.39	ug ml-1	PMID[473136]

☑ 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 NPC18857 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	442
0.1-0.2	4559
0.2-0.3	13915
0.3-0.4	11072
0.4-0.5	5022
0.5-0.6	4413
0.6-0.7	2412
0.7-0.8	694
0.8-0.85	96
0.85-0.9	37
0.9-0.95	19
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC67657
0.9861	High Similarity	NPC302578
0.9861	High Similarity	NPC128951
0.9861	High Similarity	NPC105208
0.9861	High Similarity	NPC192046
0.9861	High Similarity	NPC477227
0.9861	High Similarity	NPC185915
0.9722	High Similarity	NPC163597
0.9595	High Similarity	NPC287452
0.9583	High Similarity	NPC243027
0.9583	High Similarity	NPC196136
0.9583	High Similarity	NPC317242
0.9583	High Similarity	NPC158208
0.9444	High Similarity	NPC10476
0.9444	High Similarity	NPC192501
0.9444	High Similarity	NPC228994
0.9444	High Similarity	NPC304499
0.9444	High Similarity	NPC48795
0.9351	High Similarity	NPC478054
0.9306	High Similarity	NPC153719
0.9306	High Similarity	NPC470610
0.92	High Similarity	NPC147993
0.9079	High Similarity	NPC269333
0.9028	High Similarity	NPC251201
0.9028	High Similarity	NPC232925
0.9028	High Similarity	NPC63588
0.8889	High Similarity	NPC66407
0.8889	High Similarity	NPC477820
0.8889	High Similarity	NPC107919
0.8889	High Similarity	NPC470833
0.8875	High Similarity	NPC266651
0.8831	High Similarity	NPC81074
0.8831	High Similarity	NPC477282
0.8765	High Similarity	NPC121981
0.875	High Similarity	NPC474756
0.8734	High Similarity	NPC60018
0.8734	High Similarity	NPC475388
0.8734	High Similarity	NPC154043
0.8734	High Similarity	NPC202688
0.8718	High Similarity	NPC16449
0.8667	High Similarity	NPC475458
0.8649	High Similarity	NPC187471
0.8649	High Similarity	NPC252182
0.8649	High Similarity	NPC127094
0.8649	High Similarity	NPC470071
0.8649	High Similarity	NPC1340
0.8625	High Similarity	NPC85095
0.8625	High Similarity	NPC211135
0.8625	High Similarity	NPC216420
0.8611	High Similarity	NPC63190
0.8571	High Similarity	NPC11907
0.8571	High Similarity	NPC133596
0.8571	High Similarity	NPC474574
0.8571	High Similarity	NPC476233
0.8571	High Similarity	NPC64081
0.8519	High Similarity	NPC255882
0.8519	High Similarity	NPC320824
0.8514	High Similarity	NPC231945
0.8514	High Similarity	NPC192192
0.8472	Intermediate Similarity	NPC44122
0.8452	Intermediate Similarity	NPC109744
0.8442	Intermediate Similarity	NPC470145
0.8442	Intermediate Similarity	NPC477601
0.8442	Intermediate Similarity	NPC473916
0.8442	Intermediate Similarity	NPC477602
0.8395	Intermediate Similarity	NPC232023
0.8378	Intermediate Similarity	NPC299948
0.8378	Intermediate Similarity	NPC470830
0.8378	Intermediate Similarity	NPC129829
0.8378	Intermediate Similarity	NPC254037
0.8378	Intermediate Similarity	NPC241085
0.8372	Intermediate Similarity	NPC277774
0.8353	Intermediate Similarity	NPC473956
0.8353	Intermediate Similarity	NPC475751
0.8333	Intermediate Similarity	NPC128475
0.8333	Intermediate Similarity	NPC243469
0.8333	Intermediate Similarity	NPC190827
0.8333	Intermediate Similarity	NPC475943
0.8333	Intermediate Similarity	NPC472946
0.8313	Intermediate Similarity	NPC471240
0.8312	Intermediate Similarity	NPC139765
0.8312	Intermediate Similarity	NPC231680
0.8312	Intermediate Similarity	NPC91387
0.8312	Intermediate Similarity	NPC131584
0.8312	Intermediate Similarity	NPC270306
0.8256	Intermediate Similarity	NPC36372
0.8256	Intermediate Similarity	NPC293609
0.8243	Intermediate Similarity	NPC472741
0.8228	Intermediate Similarity	NPC471045
0.8228	Intermediate Similarity	NPC471769
0.8214	Intermediate Similarity	NPC186145
0.8214	Intermediate Similarity	NPC474657
0.8214	Intermediate Similarity	NPC263802
0.8214	Intermediate Similarity	NPC210658
0.8214	Intermediate Similarity	NPC5943
0.8214	Intermediate Similarity	NPC161928
0.8194	Intermediate Similarity	NPC159654
0.8194	Intermediate Similarity	NPC118937
0.8194	Intermediate Similarity	NPC167995
0.8194	Intermediate Similarity	NPC281540
0.8193	Intermediate Similarity	NPC273290
0.8193	Intermediate Similarity	NPC232044
0.8182	Intermediate Similarity	NPC92196
0.8158	Intermediate Similarity	NPC157422
0.8158	Intermediate Similarity	NPC157777
0.8158	Intermediate Similarity	NPC100586
0.8158	Intermediate Similarity	NPC109457
0.8158	Intermediate Similarity	NPC131506
0.814	Intermediate Similarity	NPC223143
0.814	Intermediate Similarity	NPC279329
0.8133	Intermediate Similarity	NPC99264
0.8125	Intermediate Similarity	NPC476176
0.8118	Intermediate Similarity	NPC475664
0.8108	Intermediate Similarity	NPC48079
0.8108	Intermediate Similarity	NPC473230
0.8108	Intermediate Similarity	NPC475884
0.8095	Intermediate Similarity	NPC155531
0.8095	Intermediate Similarity	NPC472272
0.8095	Intermediate Similarity	NPC476727
0.8095	Intermediate Similarity	NPC476726
0.8095	Intermediate Similarity	NPC6605
0.8095	Intermediate Similarity	NPC215968
0.8095	Intermediate Similarity	NPC131365
0.8095	Intermediate Similarity	NPC201273
0.809	Intermediate Similarity	NPC473287
0.8072	Intermediate Similarity	NPC227260
0.8068	Intermediate Similarity	NPC3538
0.8068	Intermediate Similarity	NPC477224
0.8068	Intermediate Similarity	NPC309866
0.8068	Intermediate Similarity	NPC113500
0.8056	Intermediate Similarity	NPC114891
0.8056	Intermediate Similarity	NPC236099
0.8056	Intermediate Similarity	NPC209686
0.8056	Intermediate Similarity	NPC249078
0.8052	Intermediate Similarity	NPC472341
0.8052	Intermediate Similarity	NPC473238
0.8049	Intermediate Similarity	NPC121121
0.8049	Intermediate Similarity	NPC470611
0.8046	Intermediate Similarity	NPC473066
0.8026	Intermediate Similarity	NPC282454
0.8025	Intermediate Similarity	NPC470609
0.8025	Intermediate Similarity	NPC71535
0.8025	Intermediate Similarity	NPC78545
0.8025	Intermediate Similarity	NPC474714
0.8023	Intermediate Similarity	NPC102725
0.8023	Intermediate Similarity	NPC228059
0.8023	Intermediate Similarity	NPC20822
0.8023	Intermediate Similarity	NPC473472
0.8	Intermediate Similarity	NPC477600
0.8	Intermediate Similarity	NPC477819
0.8	Intermediate Similarity	NPC477817
0.8	Intermediate Similarity	NPC31828
0.7976	Intermediate Similarity	NPC290612
0.7973	Intermediate Similarity	NPC142712
0.7955	Intermediate Similarity	NPC311246
0.7955	Intermediate Similarity	NPC182740
0.7955	Intermediate Similarity	NPC122083
0.7955	Intermediate Similarity	NPC256104
0.7955	Intermediate Similarity	NPC211845
0.7955	Intermediate Similarity	NPC167644
0.7952	Intermediate Similarity	NPC69953
0.7952	Intermediate Similarity	NPC111582
0.7952	Intermediate Similarity	NPC477285
0.7952	Intermediate Similarity	NPC470070
0.7949	Intermediate Similarity	NPC477508
0.7949	Intermediate Similarity	NPC470151
0.7945	Intermediate Similarity	NPC94897
0.7927	Intermediate Similarity	NPC469745
0.7922	Intermediate Similarity	NPC473552
0.7922	Intermediate Similarity	NPC324984
0.7922	Intermediate Similarity	NPC477823
0.7922	Intermediate Similarity	NPC323900
0.7922	Intermediate Similarity	NPC477821
0.7922	Intermediate Similarity	NPC477822
0.7922	Intermediate Similarity	NPC478103
0.7917	Intermediate Similarity	NPC71460
0.7917	Intermediate Similarity	NPC218585
0.7917	Intermediate Similarity	NPC148174
0.7907	Intermediate Similarity	NPC473436
0.7907	Intermediate Similarity	NPC281004
0.7882	Intermediate Similarity	NPC145245
0.7882	Intermediate Similarity	NPC477283
0.7875	Intermediate Similarity	NPC171658
0.7865	Intermediate Similarity	NPC473503
0.7865	Intermediate Similarity	NPC475325
0.7857	Intermediate Similarity	NPC256567
0.7857	Intermediate Similarity	NPC50438
0.7848	Intermediate Similarity	NPC472952
0.7848	Intermediate Similarity	NPC472950
0.7841	Intermediate Similarity	NPC204881
0.7841	Intermediate Similarity	NPC473830
0.7841	Intermediate Similarity	NPC5632
0.7841	Intermediate Similarity	NPC59006
0.7841	Intermediate Similarity	NPC219516
0.7841	Intermediate Similarity	NPC149966
0.7838	Intermediate Similarity	NPC41577
0.7838	Intermediate Similarity	NPC473276
0.7838	Intermediate Similarity	NPC260116
0.7838	Intermediate Similarity	NPC474380
0.7831	Intermediate Similarity	NPC296734

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 NPC18857 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	430
0.1-0.2	4488
0.2-0.3	2940
0.3-0.4	725
0.4-0.5	253
0.5-0.6	201
0.6-0.7	90
0.7-0.8	21
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD4267	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD4787	Phase 1
0.759	Intermediate Similarity	NPD6928	Phase 2
0.7561	Intermediate Similarity	NPD6118	Approved
0.7561	Intermediate Similarity	NPD6114	Approved
0.7561	Intermediate Similarity	NPD6697	Approved
0.7561	Intermediate Similarity	NPD6115	Approved
0.7439	Intermediate Similarity	NPD6116	Phase 1
0.7381	Intermediate Similarity	NPD7525	Registered
0.7363	Intermediate Similarity	NPD8171	Discontinued
0.7317	Intermediate Similarity	NPD6117	Approved
0.725	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD371	Approved
0.7195	Intermediate Similarity	NPD3703	Phase 2
0.7125	Intermediate Similarity	NPD4245	Approved
0.7125	Intermediate Similarity	NPD4244	Approved
0.7073	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3698	Phase 2
0.7	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5360	Phase 3
0.6875	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4789	Approved
0.6634	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7524	Approved
0.6596	Remote Similarity	NPD6700	Approved
0.6596	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4748	Discontinued
0.6526	Remote Similarity	NPD6702	Approved
0.6526	Remote Similarity	NPD6703	Approved
0.6512	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD7991	Discontinued
0.6484	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4634	Approved
0.6455	Remote Similarity	NPD7516	Approved
0.6452	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4758	Discontinued
0.6413	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6931	Approved
0.6404	Remote Similarity	NPD6930	Phase 2
0.6395	Remote Similarity	NPD3702	Approved
0.6395	Remote Similarity	NPD6942	Approved
0.6395	Remote Similarity	NPD7339	Approved
0.6374	Remote Similarity	NPD6695	Phase 3
0.6374	Remote Similarity	NPD4788	Approved
0.6364	Remote Similarity	NPD7328	Approved
0.6364	Remote Similarity	NPD4755	Approved
0.6364	Remote Similarity	NPD5364	Discontinued
0.6364	Remote Similarity	NPD7327	Approved
0.6364	Remote Similarity	NPD3671	Phase 1
0.6337	Remote Similarity	NPD4159	Approved
0.6322	Remote Similarity	NPD6933	Approved
0.631	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD6929	Approved
0.6292	Remote Similarity	NPD7645	Phase 2
0.6289	Remote Similarity	NPD4202	Approved
0.6265	Remote Similarity	NPD6705	Phase 1
0.625	Remote Similarity	NPD6932	Approved
0.6238	Remote Similarity	NPD4696	Approved
0.6238	Remote Similarity	NPD5285	Approved
0.6238	Remote Similarity	NPD5286	Approved
0.6238	Remote Similarity	NPD4700	Approved
0.6235	Remote Similarity	NPD6081	Approved
0.6235	Remote Similarity	NPD4243	Approved
0.6235	Remote Similarity	NPD5777	Approved
0.6195	Remote Similarity	NPD8379	Approved
0.6195	Remote Similarity	NPD8378	Approved
0.6195	Remote Similarity	NPD8296	Approved
0.6195	Remote Similarity	NPD8335	Approved
0.6195	Remote Similarity	NPD8380	Approved
0.6186	Remote Similarity	NPD8035	Phase 2
0.6186	Remote Similarity	NPD8034	Phase 2
0.6176	Remote Similarity	NPD1700	Approved
0.6139	Remote Similarity	NPD7638	Approved
0.6117	Remote Similarity	NPD5224	Approved
0.6117	Remote Similarity	NPD5211	Phase 2
0.6117	Remote Similarity	NPD4633	Approved
0.6117	Remote Similarity	NPD5225	Approved
0.6117	Remote Similarity	NPD5226	Approved
0.6111	Remote Similarity	NPD6683	Phase 2
0.6106	Remote Similarity	NPD8377	Approved
0.6106	Remote Similarity	NPD8294	Approved
0.6105	Remote Similarity	NPD7750	Discontinued
0.6095	Remote Similarity	NPD5739	Approved
0.6095	Remote Similarity	NPD7128	Approved
0.6095	Remote Similarity	NPD6675	Approved
0.6095	Remote Similarity	NPD6402	Approved
0.6092	Remote Similarity	NPD6924	Approved
0.6092	Remote Similarity	NPD6926	Approved
0.6092	Remote Similarity	NPD1811	Approved
0.6092	Remote Similarity	NPD1810	Approved
0.6092	Remote Similarity	NPD4785	Approved
0.6092	Remote Similarity	NPD4784	Approved
0.6078	Remote Similarity	NPD8418	Phase 2
0.6078	Remote Similarity	NPD7639	Approved
0.6078	Remote Similarity	NPD7640	Approved
0.6067	Remote Similarity	NPD5776	Phase 2
0.6067	Remote Similarity	NPD6925	Approved
0.6064	Remote Similarity	NPD6893	Approved
0.6058	Remote Similarity	NPD5175	Approved
0.6058	Remote Similarity	NPD5174	Approved
0.6053	Remote Similarity	NPD8033	Approved
0.6044	Remote Similarity	NPD7514	Phase 3
0.6024	Remote Similarity	NPD4224	Phase 2
0.6019	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD7145	Approved
0.6	Remote Similarity	NPD8133	Approved
0.6	Remote Similarity	NPD5141	Approved
0.6	Remote Similarity	NPD8308	Discontinued
0.5981	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD6881	Approved
0.5981	Remote Similarity	NPD6899	Approved
0.5981	Remote Similarity	NPD7320	Approved
0.5979	Remote Similarity	NPD4753	Phase 2
0.5979	Remote Similarity	NPD5328	Approved
0.5972	Remote Similarity	NPD384	Approved
0.5972	Remote Similarity	NPD385	Approved
0.5965	Remote Similarity	NPD6319	Approved
0.5965	Remote Similarity	NPD6054	Approved
0.5965	Remote Similarity	NPD6059	Approved
0.5962	Remote Similarity	NPD7632	Discontinued
0.5957	Remote Similarity	NPD4786	Approved
0.5943	Remote Similarity	NPD4768	Approved
0.5943	Remote Similarity	NPD4767	Approved
0.5926	Remote Similarity	NPD6372	Approved
0.5926	Remote Similarity	NPD6373	Approved
0.5926	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD8297	Approved
0.5905	Remote Similarity	NPD4754	Approved
0.5888	Remote Similarity	NPD6412	Phase 2
0.5888	Remote Similarity	NPD5701	Approved
0.5888	Remote Similarity	NPD5697	Approved
0.5882	Remote Similarity	NPD7920	Phase 3
0.5882	Remote Similarity	NPD7919	Phase 3
0.5872	Remote Similarity	NPD6883	Approved
0.5872	Remote Similarity	NPD7290	Approved
0.5872	Remote Similarity	NPD7102	Approved
0.587	Remote Similarity	NPD7509	Discontinued
0.587	Remote Similarity	NPD7332	Phase 2
0.5862	Remote Similarity	NPD6370	Approved
0.5859	Remote Similarity	NPD6079	Approved
0.5859	Remote Similarity	NPD7087	Discontinued
0.5847	Remote Similarity	NPD7507	Approved
0.5843	Remote Similarity	NPD4190	Phase 3
0.5843	Remote Similarity	NPD5275	Approved
0.5833	Remote Similarity	NPD5128	Approved
0.5833	Remote Similarity	NPD7319	Approved
0.5833	Remote Similarity	NPD4730	Approved
0.5833	Remote Similarity	NPD4729	Approved
0.5833	Remote Similarity	NPD386	Approved
0.5833	Remote Similarity	NPD388	Approved
0.5833	Remote Similarity	NPD3618	Phase 1
0.5825	Remote Similarity	NPD8088	Phase 1
0.5818	Remote Similarity	NPD6617	Approved
0.5818	Remote Similarity	NPD6649	Approved
0.5818	Remote Similarity	NPD6869	Approved
0.5818	Remote Similarity	NPD8130	Phase 1
0.5818	Remote Similarity	NPD6650	Approved
0.5818	Remote Similarity	NPD6847	Approved
0.5806	Remote Similarity	NPD6898	Phase 1
0.5806	Remote Similarity	NPD6902	Approved
0.5789	Remote Similarity	NPD3665	Phase 1
0.5789	Remote Similarity	NPD3666	Approved
0.5789	Remote Similarity	NPD3133	Approved
0.578	Remote Similarity	NPD6014	Approved
0.578	Remote Similarity	NPD6012	Approved
0.578	Remote Similarity	NPD6013	Approved
0.5776	Remote Similarity	NPD6016	Approved
0.5776	Remote Similarity	NPD6015	Approved
0.5776	Remote Similarity	NPD7503	Approved
0.5766	Remote Similarity	NPD6882	Approved
0.5763	Remote Similarity	NPD7492	Approved
0.5761	Remote Similarity	NPD4195	Approved
0.5752	Remote Similarity	NPD6940	Discontinued
0.575	Remote Similarity	NPD7736	Approved
0.5747	Remote Similarity	NPD2254	Approved
0.5747	Remote Similarity	NPD2687	Approved
0.5747	Remote Similarity	NPD2686	Approved
0.5745	Remote Similarity	NPD3667	Approved
0.5728	Remote Similarity	NPD6084	Phase 2
0.5728	Remote Similarity	NPD6083	Phase 2
0.5727	Remote Similarity	NPD5249	Phase 3
0.5727	Remote Similarity	NPD5250	Approved
0.5727	Remote Similarity	NPD5247	Approved
0.5727	Remote Similarity	NPD5251	Approved
0.5727	Remote Similarity	NPD5248	Approved
0.5726	Remote Similarity	NPD5988	Approved
0.5714	Remote Similarity	NPD6616	Approved
0.5702	Remote Similarity	NPD6009	Approved
0.5688	Remote Similarity	NPD8174	Phase 2
0.5688	Remote Similarity	NPD6011	Approved
0.5686	Remote Similarity	NPD5210	Approved
0.5686	Remote Similarity	NPD4629	Approved
0.5682	Remote Similarity	NPD7152	Approved
0.5682	Remote Similarity	NPD7151	Approved
0.5682	Remote Similarity	NPD7150	Approved
0.5676	Remote Similarity	NPD5216	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