NPASS Compound

Structure

CID180725 OpenBabel06191715552D 38 38 0 0 1 0 0 0 0 0999 V2000 12.1244 18.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 18.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 18.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 17.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 16.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 15.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 15.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 14.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 12.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 9.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 5.1962 8.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 6.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 1 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 6.0622 7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 18 23 1 0 0 0 0 18 24 1 0 0 0 0 19 24 1 0 0 0 0 19 25 1 0 0 0 0 20 25 1 0 0 0 0 20 26 1 0 0 0 0 21 26 1 0 0 0 0 21 27 1 0 0 0 0 22 27 1 0 0 0 0 23 31 1 1 0 0 0 24 32 1 6 0 0 0 25 33 1 6 0 0 0 26 34 1 6 0 0 0 27 35 1 6 0 0 0 28 29 1 0 0 0 0 28 36 1 1 0 0 0 29 22 1 1 0 0 0 29 38 1 0 0 0 0 30 37 2 0 0 0 0 30 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	544.4
Volume:	583.928
LogP:	4.331
LogD:	3.384
LogS:	-4.916
# Rotatable Bonds:	24
TPSA:	144.52
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	1
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.088
Synthetic Accessibility Score:	4.391
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
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:	-5.194
MDCK Permeability:	2.7964779292233288e-05
Pgp-inhibitor:	0.3
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.139
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.086
Plasma Protein Binding (PPB):	94.76193237304688%
Volume Distribution (VD):	1.055
Pgp-substrate:	3.14711332321167%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.161
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.078
CYP2C9-inhibitor:	0.294
CYP2C9-substrate:	0.347
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.015
CYP3A4-inhibitor:	0.317
CYP3A4-substrate:	0.041

ADMET: Excretion

Clearance (CL):	10.578
Half-life (T1/2):	0.825

ADMET: Toxicity

hERG Blockers:	0.157
Human Hepatotoxicity (H-HT):	0.328
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.957
Carcinogencity:	0.509
Eye Corrosion:	0.051
Eye Irritation:	0.134
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC180725

Natural Product ID:	NPC180725
*Common Name:**	Cryptocaryol C
IUPAC Name:	(2S,3S)-3-hydroxy-2-[(2S,4S,6S,8S,10R)-2,4,6,8,10-pentahydroxypentacosyl]-2,3-dihydropyran-6-one
Synonyms:	Cryptocaryol C
Standard InCHIKey:	LCODPNNXGVNGAW-KVARLTFLSA-N
Standard InCHI:	InChI=1S/C30H56O8/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-23(31)18-24(32)19-25(33)20-26(34)21-27(35)22-29-28(36)16-17-30(37)38-29/h16-17,23-29,31-36H,2-15,18-22H2,1H3/t23-,24+,25+,26+,27+,28+,29+/m1/s1
SMILES:	CCCCCCCCCCCCCCC[C@H](C[C@@H](C[C@@H](C[C@@H](C[C@@H](C[C@@H]1OC(=O)C=C[C@@H]1O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1784374
PubChem CID:	54586934
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

*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
NPO33207	cryptocarya sp.	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21539301]
NPO29906	Cryptocarya	Genus	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21539301]

☑ 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
EC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4409	Individual Protein	Programmed cell death protein 4	Homo sapiens	EC50	=	1600.0	nM	PMID[536920]

☑ 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 NPC180725 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	181
0.1-0.2	1849
0.2-0.3	5621
0.3-0.4	15240
0.4-0.5	12279
0.5-0.6	5220
0.6-0.7	1805
0.7-0.8	442
0.8-0.85	34
0.85-0.9	11
0.9-0.95	8
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9865	High Similarity	NPC133226
0.9865	High Similarity	NPC470147
0.9863	High Similarity	NPC248775
0.973	High Similarity	NPC470148
0.973	High Similarity	NPC470149
0.9726	High Similarity	NPC474026
0.9189	High Similarity	NPC327041
0.9189	High Similarity	NPC285840
0.9178	High Similarity	NPC185186
0.9178	High Similarity	NPC327383
0.9041	High Similarity	NPC475762
0.8961	High Similarity	NPC1180
0.8947	High Similarity	NPC475711
0.8889	High Similarity	NPC208473
0.8734	High Similarity	NPC469469
0.8701	High Similarity	NPC233071
0.8667	High Similarity	NPC329914
0.8667	High Similarity	NPC329890
0.8642	High Similarity	NPC473308
0.863	High Similarity	NPC475760
0.8571	High Similarity	NPC188860
0.8519	High Similarity	NPC142111
0.8519	High Similarity	NPC473315
0.8481	Intermediate Similarity	NPC139712
0.8471	Intermediate Similarity	NPC177668
0.8471	Intermediate Similarity	NPC3952
0.84	Intermediate Similarity	NPC476012
0.84	Intermediate Similarity	NPC476037
0.8395	Intermediate Similarity	NPC251026
0.8356	Intermediate Similarity	NPC201356
0.8353	Intermediate Similarity	NPC133450
0.825	Intermediate Similarity	NPC473947
0.8219	Intermediate Similarity	NPC19769
0.8219	Intermediate Similarity	NPC96414
0.8182	Intermediate Similarity	NPC256368
0.8125	Intermediate Similarity	NPC477314
0.8101	Intermediate Similarity	NPC326661
0.8095	Intermediate Similarity	NPC471494
0.8082	Intermediate Similarity	NPC25747
0.8082	Intermediate Similarity	NPC148233
0.8068	Intermediate Similarity	NPC238090
0.8068	Intermediate Similarity	NPC472195
0.8068	Intermediate Similarity	NPC472196
0.8049	Intermediate Similarity	NPC8538
0.8049	Intermediate Similarity	NPC184208
0.8049	Intermediate Similarity	NPC315731
0.8046	Intermediate Similarity	NPC473311
0.8023	Intermediate Similarity	NPC233551
0.8023	Intermediate Similarity	NPC20339
0.8023	Intermediate Similarity	NPC280621
0.8023	Intermediate Similarity	NPC48338
0.8023	Intermediate Similarity	NPC40376
0.8023	Intermediate Similarity	NPC21208
0.8023	Intermediate Similarity	NPC470137
0.8	Intermediate Similarity	NPC311163
0.8	Intermediate Similarity	NPC47937
0.7978	Intermediate Similarity	NPC159698
0.7976	Intermediate Similarity	NPC160517
0.7976	Intermediate Similarity	NPC186155
0.7976	Intermediate Similarity	NPC78673
0.7912	Intermediate Similarity	NPC475332
0.7907	Intermediate Similarity	NPC178215
0.7882	Intermediate Similarity	NPC477014
0.7882	Intermediate Similarity	NPC329615
0.7882	Intermediate Similarity	NPC471567
0.7882	Intermediate Similarity	NPC120398
0.7882	Intermediate Similarity	NPC470124
0.7882	Intermediate Similarity	NPC322529
0.7882	Intermediate Similarity	NPC329838
0.7882	Intermediate Similarity	NPC477013
0.7882	Intermediate Similarity	NPC182383
0.7867	Intermediate Similarity	NPC124586
0.7867	Intermediate Similarity	NPC276299
0.7867	Intermediate Similarity	NPC146811
0.7841	Intermediate Similarity	NPC473904
0.7841	Intermediate Similarity	NPC239517
0.7816	Intermediate Similarity	NPC89001
0.7816	Intermediate Similarity	NPC473905
0.7816	Intermediate Similarity	NPC320458
0.7808	Intermediate Similarity	NPC26810
0.7802	Intermediate Similarity	NPC472995
0.7791	Intermediate Similarity	NPC231096
0.7791	Intermediate Similarity	NPC134865
0.7791	Intermediate Similarity	NPC103523
0.7791	Intermediate Similarity	NPC114694
0.7791	Intermediate Similarity	NPC61527
0.7791	Intermediate Similarity	NPC279267
0.7791	Intermediate Similarity	NPC171174
0.7791	Intermediate Similarity	NPC475581
0.7791	Intermediate Similarity	NPC62118
0.7791	Intermediate Similarity	NPC240695
0.7791	Intermediate Similarity	NPC142117
0.7791	Intermediate Similarity	NPC477015
0.7791	Intermediate Similarity	NPC107717
0.7791	Intermediate Similarity	NPC69082
0.7791	Intermediate Similarity	NPC232555
0.7778	Intermediate Similarity	NPC477203
0.7765	Intermediate Similarity	NPC266718
0.7765	Intermediate Similarity	NPC474251
0.7765	Intermediate Similarity	NPC475035
0.7765	Intermediate Similarity	NPC156804
0.7765	Intermediate Similarity	NPC163093
0.7753	Intermediate Similarity	NPC469410
0.7727	Intermediate Similarity	NPC477016
0.7727	Intermediate Similarity	NPC81778
0.7727	Intermediate Similarity	NPC42598
0.7727	Intermediate Similarity	NPC477011
0.7727	Intermediate Similarity	NPC20621
0.7727	Intermediate Similarity	NPC318963
0.7727	Intermediate Similarity	NPC477017
0.7727	Intermediate Similarity	NPC40066
0.7727	Intermediate Similarity	NPC139418
0.7727	Intermediate Similarity	NPC473504
0.7727	Intermediate Similarity	NPC91067
0.7727	Intermediate Similarity	NPC93794
0.7722	Intermediate Similarity	NPC477085
0.7722	Intermediate Similarity	NPC284006
0.7722	Intermediate Similarity	NPC470435
0.7717	Intermediate Similarity	NPC40812
0.7701	Intermediate Similarity	NPC118077
0.7701	Intermediate Similarity	NPC475037
0.7701	Intermediate Similarity	NPC20533
0.7701	Intermediate Similarity	NPC476583
0.7701	Intermediate Similarity	NPC475186
0.7701	Intermediate Similarity	NPC258068
0.7674	Intermediate Similarity	NPC66346
0.7674	Intermediate Similarity	NPC286338
0.7674	Intermediate Similarity	NPC82795
0.7674	Intermediate Similarity	NPC132496
0.7674	Intermediate Similarity	NPC473651
0.7674	Intermediate Similarity	NPC283085
0.7674	Intermediate Similarity	NPC107986
0.7674	Intermediate Similarity	NPC103284
0.7674	Intermediate Similarity	NPC473669
0.7674	Intermediate Similarity	NPC473478
0.7674	Intermediate Similarity	NPC223871
0.7674	Intermediate Similarity	NPC475034
0.7674	Intermediate Similarity	NPC110710
0.7674	Intermediate Similarity	NPC231009
0.7674	Intermediate Similarity	NPC1083
0.7671	Intermediate Similarity	NPC26223
0.7667	Intermediate Similarity	NPC109406
0.7662	Intermediate Similarity	NPC63873
0.7654	Intermediate Similarity	NPC477202
0.7654	Intermediate Similarity	NPC469880
0.7647	Intermediate Similarity	NPC253801
0.7647	Intermediate Similarity	NPC44261
0.7647	Intermediate Similarity	NPC315559
0.7634	Intermediate Similarity	NPC475653
0.7625	Intermediate Similarity	NPC477315
0.7625	Intermediate Similarity	NPC477309
0.7625	Intermediate Similarity	NPC477316
0.7625	Intermediate Similarity	NPC477304
0.7625	Intermediate Similarity	NPC477305
0.7625	Intermediate Similarity	NPC477312
0.7625	Intermediate Similarity	NPC477308
0.7625	Intermediate Similarity	NPC477313
0.7625	Intermediate Similarity	NPC315843
0.7625	Intermediate Similarity	NPC107654
0.7619	Intermediate Similarity	NPC297440
0.7614	Intermediate Similarity	NPC61257
0.7614	Intermediate Similarity	NPC39754
0.7614	Intermediate Similarity	NPC274446
0.7614	Intermediate Similarity	NPC172821
0.7614	Intermediate Similarity	NPC191929
0.7614	Intermediate Similarity	NPC151403
0.7614	Intermediate Similarity	NPC320569
0.7614	Intermediate Similarity	NPC242364
0.7614	Intermediate Similarity	NPC133730
0.7614	Intermediate Similarity	NPC261952
0.7614	Intermediate Similarity	NPC81045
0.7614	Intermediate Similarity	NPC287164
0.7614	Intermediate Similarity	NPC100454
0.7614	Intermediate Similarity	NPC234077
0.7614	Intermediate Similarity	NPC169511
0.7614	Intermediate Similarity	NPC171135
0.7609	Intermediate Similarity	NPC255410
0.7609	Intermediate Similarity	NPC173329
0.7609	Intermediate Similarity	NPC288350
0.76	Intermediate Similarity	NPC308457
0.7595	Intermediate Similarity	NPC477086
0.7595	Intermediate Similarity	NPC477087
0.7595	Intermediate Similarity	NPC293114
0.759	Intermediate Similarity	NPC86971
0.759	Intermediate Similarity	NPC226226
0.759	Intermediate Similarity	NPC55304
0.7586	Intermediate Similarity	NPC309211
0.7586	Intermediate Similarity	NPC282815
0.7586	Intermediate Similarity	NPC308412
0.7586	Intermediate Similarity	NPC473840
0.7586	Intermediate Similarity	NPC134807
0.7586	Intermediate Similarity	NPC132940
0.7586	Intermediate Similarity	NPC293136
0.7586	Intermediate Similarity	NPC219498
0.7586	Intermediate Similarity	NPC241360
0.7586	Intermediate Similarity	NPC473687
0.7586	Intermediate Similarity	NPC219652
0.7586	Intermediate Similarity	NPC134885
0.7586	Intermediate Similarity	NPC112685
0.7586	Intermediate Similarity	NPC25703

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 NPC180725 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	2465
0.2-0.3	3730
0.3-0.4	2079
0.4-0.5	545
0.5-0.6	139
0.6-0.7	31
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8046	Intermediate Similarity	NPD7838	Discovery
0.7841	Intermediate Similarity	NPD46	Approved
0.7841	Intermediate Similarity	NPD6698	Approved
0.7474	Intermediate Similarity	NPD5344	Discontinued
0.7447	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7983	Approved
0.701	Intermediate Similarity	NPD6648	Approved
0.6778	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4250	Approved
0.6739	Remote Similarity	NPD4251	Approved
0.6705	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4249	Approved
0.6602	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6371	Approved
0.6566	Remote Similarity	NPD4225	Approved
0.6538	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3197	Phase 1
0.6494	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4271	Approved
0.6477	Remote Similarity	NPD4268	Approved
0.6364	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5785	Approved
0.6333	Remote Similarity	NPD4822	Approved
0.6333	Remote Similarity	NPD4820	Approved
0.6333	Remote Similarity	NPD4821	Approved
0.6333	Remote Similarity	NPD4819	Approved
0.6304	Remote Similarity	NPD7154	Phase 3
0.6283	Remote Similarity	NPD7503	Approved
0.6282	Remote Similarity	NPD9119	Approved
0.6282	Remote Similarity	NPD6109	Phase 1
0.6282	Remote Similarity	NPD69	Approved
0.6224	Remote Similarity	NPD5779	Approved
0.6224	Remote Similarity	NPD5778	Approved
0.622	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7839	Suspended
0.618	Remote Similarity	NPD4756	Discovery
0.6176	Remote Similarity	NPD7639	Approved
0.6176	Remote Similarity	NPD7640	Approved
0.6174	Remote Similarity	NPD7830	Approved
0.6174	Remote Similarity	NPD7829	Approved
0.617	Remote Similarity	NPD5363	Approved
0.6154	Remote Similarity	NPD9118	Approved
0.614	Remote Similarity	NPD8513	Phase 3
0.6129	Remote Similarity	NPD6110	Phase 1
0.6122	Remote Similarity	NPD7637	Suspended
0.6111	Remote Similarity	NPD6421	Discontinued
0.6078	Remote Similarity	NPD7638	Approved
0.6071	Remote Similarity	NPD7505	Discontinued
0.6071	Remote Similarity	NPD7115	Discovery
0.6034	Remote Similarity	NPD7642	Approved
0.6018	Remote Similarity	NPD7328	Approved
0.6018	Remote Similarity	NPD7327	Approved
0.6	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD8515	Approved
0.6	Remote Similarity	NPD8033	Approved
0.6	Remote Similarity	NPD1407	Approved
0.6	Remote Similarity	NPD6053	Discontinued
0.6	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8517	Approved
0.5965	Remote Similarity	NPD7516	Approved
0.5957	Remote Similarity	NPD5362	Discontinued
0.5941	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD8377	Approved
0.5913	Remote Similarity	NPD8294	Approved
0.5877	Remote Similarity	NPD7641	Discontinued
0.5876	Remote Similarity	NPD7524	Approved
0.5862	Remote Similarity	NPD8444	Approved
0.5862	Remote Similarity	NPD8296	Approved
0.5862	Remote Similarity	NPD8378	Approved
0.5862	Remote Similarity	NPD8335	Approved
0.5862	Remote Similarity	NPD8380	Approved
0.5862	Remote Similarity	NPD8379	Approved
0.5851	Remote Similarity	NPD4270	Approved
0.5851	Remote Similarity	NPD6435	Approved
0.5851	Remote Similarity	NPD4269	Approved
0.5806	Remote Similarity	NPD4252	Approved
0.5798	Remote Similarity	NPD8273	Phase 1
0.5789	Remote Similarity	NPD5331	Approved
0.5789	Remote Similarity	NPD5332	Approved
0.5789	Remote Similarity	NPD7500	Approved
0.5773	Remote Similarity	NPD5786	Approved
0.5769	Remote Similarity	NPD3196	Approved
0.5769	Remote Similarity	NPD3195	Phase 2
0.5769	Remote Similarity	NPD3194	Approved
0.5769	Remote Similarity	NPD4266	Approved
0.5769	Remote Similarity	NPD3730	Approved
0.5769	Remote Similarity	NPD3728	Approved
0.5766	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.575	Remote Similarity	NPD8074	Phase 3
0.5745	Remote Similarity	NPD4790	Discontinued
0.5729	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD5209	Approved
0.5667	Remote Similarity	NPD8451	Approved
0.5667	Remote Similarity	NPD7507	Approved
0.5644	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD3172	Approved
0.5638	Remote Similarity	NPD5368	Approved
0.5625	Remote Similarity	NPD6695	Phase 3
0.562	Remote Similarity	NPD8448	Approved
0.5607	Remote Similarity	NPD7632	Discontinued
0.5604	Remote Similarity	NPD8039	Approved
0.56	Remote Similarity	NPD1695	Approved
0.56	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.56	Remote Similarity	NPD5370	Suspended
0.56	Remote Similarity	NPD6101	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