NPASS Compound

Structure

NPC10721 OpenBabel07101719152D 42 45 0 0 1 0 0 0 0 0999 V2000 7.8308 2.3831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5305 4.5384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8136 3.5126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2521 -1.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5903 0.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 -0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7169 -1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9723 2.8960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5454 3.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0989 2.4090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2404 2.9219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3670 2.4349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5086 2.9478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6352 2.4609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7767 2.9738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9033 2.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4921 -0.7376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4412 -3.1110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7541 -2.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0938 -4.1369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6870 3.0256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3011 -1.3254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 0.0259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4452 -3.2006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 -2.2764 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 -1.3254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8884 -1.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8884 1.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9921 -2.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 -0.9999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8584 0.5129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7019 2.0257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8584 -0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7468 -0.9740 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 -0.1073 -4.3007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7468 0.9740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5799 -3.0854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5753 1.5387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3265 -1.8813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8435 1.5128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0150 0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 33 1 0 0 0 0 7 33 1 0 0 0 0 8 10 1 0 0 0 0 9 21 2 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 16 1 0 0 0 0 16 28 1 0 0 0 0 17 22 2 0 0 0 0 17 26 1 0 0 0 0 18 24 1 0 0 0 0 19 24 2 0 0 0 0 19 27 1 0 0 0 0 20 24 1 0 0 0 0 20 36 1 0 0 0 0 21 32 1 0 0 0 0 22 29 1 0 0 0 0 23 31 1 0 0 0 0 23 34 1 6 0 0 0 25 18 1 1 0 0 0 25 26 1 0 0 0 0 25 29 1 0 0 0 0 26 34 1 1 0 0 0 27 30 1 0 0 0 0 27 34 1 6 0 0 0 28 37 2 0 0 0 0 28 42 1 0 0 0 0 29 38 2 0 0 0 0 30 33 1 0 0 0 0 30 35 1 6 0 0 0 31 35 1 1 0 0 0 31 41 1 0 0 0 0 32 39 2 0 0 0 0 32 41 1 0 0 0 0 33 35 1 0 0 0 0 34 40 1 6 0 0 0 35 42 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	145.07
Volume:	138.507
LogP:	-2.718
LogD:	-1.04
LogS:	-0.195
# Rotatable Bonds:	1
TPSA:	69.56
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.451
Synthetic Accessibility Score:	3.269
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.9
MDCK Permeability:	0.0006799382390454412
Pgp-inhibitor:	0.001
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.148
20% Bioavailability (F20%):	0.152
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.381
Plasma Protein Binding (PPB):	11.344656944274902%
Volume Distribution (VD):	0.536
Pgp-substrate:	93.25519561767578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.066
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.324
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.174
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.018

ADMET: Excretion

Clearance (CL):	5.55
Half-life (T1/2):	0.662

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.076
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.58
Skin Sensitization:	0.426
Carcinogencity:	0.154
Eye Corrosion:	0.308
Eye Irritation:	0.789
Respiratory Toxicity:	0.517

Download Data

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

Natural Product: NPC10721

Natural Product ID:	NPC10721
*Common Name:**	NFCYJOSYKJZRIJ-UHNTWSMTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NFCYJOSYKJZRIJ-UHNTWSMTSA-N
Standard InCHI:	InChI=1S/C35H52O7/c1-8-10-11-12-13-14-15-16-28(37)42-35-30(33(35,6)7)27-19-24(20-36)18-25-26(17-22(4)29(25)38)34(27,40)23(5)31(35)41-32(39)21(3)9-2/h9,17,19,23,25-27,30-31,36,40H,8,10-16,18,20H2,1-7H3/b21-9+/t23-,25-,26-,27+,30-,31-,34+,35-/m1/s1
SMILES:	CCCCCCCCCC(=O)O[C@]12[C@H]([C@@H]3C=C(C[C@@H]4[C@@H](C=C(C)C4=O)[C@]3([C@H](C)[C@H]1OC(=O)/C(=C/C)/C)O)CO)C2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375790
PubChem CID:	73351893
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

*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
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049973]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23701597]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25819096]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2978	Croton tiglium	Species	Euphorbiaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT890	Cell Line	SNU-387	Homo sapiens	IC50	>	10000.0	nM	PMID[494167]

☑ 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 NPC10721 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	241
0.1-0.2	1447
0.2-0.3	4218
0.3-0.4	6777
0.4-0.5	13861
0.5-0.6	8139
0.6-0.7	6276
0.7-0.8	1535
0.8-0.85	82
0.85-0.9	25
0.9-0.95	57
0.95-1	39

Similarity Score	Similarity Level	Natural Product ID
0.9907	High Similarity	NPC154363
0.9907	High Similarity	NPC234858
0.9907	High Similarity	NPC471127
0.9727	High Similarity	NPC329080
0.9727	High Similarity	NPC472759
0.9725	High Similarity	NPC146280
0.9725	High Similarity	NPC124676
0.972	High Similarity	NPC472757
0.964	High Similarity	NPC52839
0.9636	High Similarity	NPC156745
0.9636	High Similarity	NPC236918
0.963	High Similarity	NPC472400
0.955	High Similarity	NPC471128
0.955	High Similarity	NPC145182
0.955	High Similarity	NPC157252
0.955	High Similarity	NPC475885
0.955	High Similarity	NPC471126
0.9459	High Similarity	NPC22628
0.9459	High Similarity	NPC5991
0.9459	High Similarity	NPC275696
0.9459	High Similarity	NPC471108
0.9459	High Similarity	NPC255081
0.9459	High Similarity	NPC5989
0.9386	High Similarity	NPC145238
0.9381	High Similarity	NPC162009
0.9381	High Similarity	NPC257017
0.9369	High Similarity	NPC471125
0.9369	High Similarity	NPC171905
0.9369	High Similarity	NPC472758
0.9369	High Similarity	NPC472397
0.9298	High Similarity	NPC472399
0.9279	High Similarity	NPC156252
0.9211	High Similarity	NPC19464
0.9182	High Similarity	NPC71889
0.9123	High Similarity	NPC472401
0.9099	High Similarity	NPC474872
0.9091	High Similarity	NPC215643
0.9091	High Similarity	NPC89227
0.9091	High Similarity	NPC101825
0.9091	High Similarity	NPC170212
0.9091	High Similarity	NPC151216
0.9091	High Similarity	NPC265499
0.9091	High Similarity	NPC221511
0.9091	High Similarity	NPC17138
0.9035	High Similarity	NPC185876
0.9035	High Similarity	NPC19336
0.9027	High Similarity	NPC472760
0.9009	High Similarity	NPC474937
0.9	High Similarity	NPC174471
0.9	High Similarity	NPC474871
0.9	High Similarity	NPC96739
0.9	High Similarity	NPC260786
0.9	High Similarity	NPC475937
0.9	High Similarity	NPC158523
0.8947	High Similarity	NPC180640
0.8919	High Similarity	NPC475391
0.8909	High Similarity	NPC153036
0.8824	High Similarity	NPC270109
0.8772	High Similarity	NPC153651
0.8729	High Similarity	NPC473919
0.8729	High Similarity	NPC473709
0.8689	High Similarity	NPC476111
0.8673	High Similarity	NPC477091
0.8655	High Similarity	NPC222307
0.8649	High Similarity	NPC163004
0.8649	High Similarity	NPC273433
0.8644	High Similarity	NPC473802
0.8621	High Similarity	NPC472667
0.8583	High Similarity	NPC471940
0.8512	High Similarity	NPC236999
0.85	High Similarity	NPC471939
0.8468	Intermediate Similarity	NPC187435
0.8468	Intermediate Similarity	NPC67321
0.8455	Intermediate Similarity	NPC189393
0.8455	Intermediate Similarity	NPC90814
0.839	Intermediate Similarity	NPC143755
0.8347	Intermediate Similarity	NPC293112
0.8333	Intermediate Similarity	NPC469656
0.8333	Intermediate Similarity	NPC469655
0.8333	Intermediate Similarity	NPC474846
0.8319	Intermediate Similarity	NPC310511
0.8305	Intermediate Similarity	NPC469380
0.8304	Intermediate Similarity	NPC143609
0.8291	Intermediate Similarity	NPC469684
0.8273	Intermediate Similarity	NPC476081
0.8261	Intermediate Similarity	NPC472002
0.8261	Intermediate Similarity	NPC470063
0.8246	Intermediate Similarity	NPC253906
0.8246	Intermediate Similarity	NPC257240
0.823	Intermediate Similarity	NPC306265
0.8214	Intermediate Similarity	NPC111952
0.8211	Intermediate Similarity	NPC470850
0.8205	Intermediate Similarity	NPC179626
0.8205	Intermediate Similarity	NPC471816
0.8205	Intermediate Similarity	NPC470793
0.8197	Intermediate Similarity	NPC473635
0.8189	Intermediate Similarity	NPC243902
0.8182	Intermediate Similarity	NPC11895
0.8182	Intermediate Similarity	NPC469789
0.8167	Intermediate Similarity	NPC67569
0.816	Intermediate Similarity	NPC475139
0.816	Intermediate Similarity	NPC180902
0.8158	Intermediate Similarity	NPC475586
0.8151	Intermediate Similarity	NPC470186
0.8151	Intermediate Similarity	NPC475041
0.8145	Intermediate Similarity	NPC104382
0.8145	Intermediate Similarity	NPC470851
0.8136	Intermediate Similarity	NPC475323
0.8136	Intermediate Similarity	NPC473656
0.8125	Intermediate Similarity	NPC118911
0.812	Intermediate Similarity	NPC138303
0.812	Intermediate Similarity	NPC133677
0.812	Intermediate Similarity	NPC67290
0.8115	Intermediate Similarity	NPC81736
0.8115	Intermediate Similarity	NPC172154
0.8108	Intermediate Similarity	NPC137430
0.8108	Intermediate Similarity	NPC162973
0.8103	Intermediate Similarity	NPC152117
0.8103	Intermediate Similarity	NPC234042
0.8103	Intermediate Similarity	NPC269530
0.8099	Intermediate Similarity	NPC23786
0.8099	Intermediate Similarity	NPC470265
0.8099	Intermediate Similarity	NPC170538
0.8091	Intermediate Similarity	NPC470074
0.8091	Intermediate Similarity	NPC47024
0.8091	Intermediate Similarity	NPC474718
0.8087	Intermediate Similarity	NPC472214
0.8087	Intermediate Similarity	NPC477103
0.8087	Intermediate Similarity	NPC5103
0.8087	Intermediate Similarity	NPC472215
0.8083	Intermediate Similarity	NPC268530
0.8083	Intermediate Similarity	NPC154491
0.8083	Intermediate Similarity	NPC48692
0.8083	Intermediate Similarity	NPC4548
0.808	Intermediate Similarity	NPC471170
0.807	Intermediate Similarity	NPC308191
0.807	Intermediate Similarity	NPC469916
0.807	Intermediate Similarity	NPC472439
0.8051	Intermediate Similarity	NPC176840
0.8045	Intermediate Similarity	NPC140021
0.8036	Intermediate Similarity	NPC61442
0.8036	Intermediate Similarity	NPC8196
0.8036	Intermediate Similarity	NPC99266
0.8036	Intermediate Similarity	NPC120321
0.8034	Intermediate Similarity	NPC46269
0.8034	Intermediate Similarity	NPC106395
0.8034	Intermediate Similarity	NPC25909
0.8034	Intermediate Similarity	NPC477126
0.8034	Intermediate Similarity	NPC469454
0.8034	Intermediate Similarity	NPC469463
0.8034	Intermediate Similarity	NPC469496
0.8034	Intermediate Similarity	NPC471204
0.8033	Intermediate Similarity	NPC469352
0.8033	Intermediate Similarity	NPC469382
0.8033	Intermediate Similarity	NPC473979
0.8031	Intermediate Similarity	NPC473548
0.8031	Intermediate Similarity	NPC471136
0.8031	Intermediate Similarity	NPC100017
0.8031	Intermediate Similarity	NPC182266
0.8031	Intermediate Similarity	NPC475154
0.8031	Intermediate Similarity	NPC471137
0.8031	Intermediate Similarity	NPC476823
0.8031	Intermediate Similarity	NPC475500
0.8031	Intermediate Similarity	NPC223356
0.8018	Intermediate Similarity	NPC471412
0.8017	Intermediate Similarity	NPC4021
0.8017	Intermediate Similarity	NPC317107
0.8017	Intermediate Similarity	NPC475668
0.8017	Intermediate Similarity	NPC287311
0.8017	Intermediate Similarity	NPC470076
0.8017	Intermediate Similarity	NPC159456
0.8017	Intermediate Similarity	NPC475480
0.8017	Intermediate Similarity	NPC473921
0.8	Intermediate Similarity	NPC473636
0.8	Intermediate Similarity	NPC175186
0.8	Intermediate Similarity	NPC216478
0.8	Intermediate Similarity	NPC312536
0.8	Intermediate Similarity	NPC77689
0.8	Intermediate Similarity	NPC231529
0.8	Intermediate Similarity	NPC473839
0.8	Intermediate Similarity	NPC173905
0.8	Intermediate Similarity	NPC477102
0.8	Intermediate Similarity	NPC284828
0.8	Intermediate Similarity	NPC469370
0.8	Intermediate Similarity	NPC211093
0.8	Intermediate Similarity	NPC162495
0.8	Intermediate Similarity	NPC472216
0.8	Intermediate Similarity	NPC5475
0.7984	Intermediate Similarity	NPC475273
0.7984	Intermediate Similarity	NPC168849
0.7984	Intermediate Similarity	NPC298841
0.7983	Intermediate Similarity	NPC312824
0.7983	Intermediate Similarity	NPC473968
0.7983	Intermediate Similarity	NPC98249
0.7983	Intermediate Similarity	NPC284068
0.7983	Intermediate Similarity	NPC470493
0.7983	Intermediate Similarity	NPC13713
0.7983	Intermediate Similarity	NPC183580
0.7983	Intermediate Similarity	NPC58662
0.7983	Intermediate Similarity	NPC53396

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 NPC10721 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	1863
0.2-0.3	3610
0.3-0.4	2207
0.4-0.5	834
0.5-0.6	270
0.6-0.7	146
0.7-0.8	10
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8246	Intermediate Similarity	NPD6371	Approved
0.7857	Intermediate Similarity	NPD5344	Discontinued
0.7845	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD7115	Discovery
0.7778	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD6648	Approved
0.7522	Intermediate Similarity	NPD4225	Approved
0.7521	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7639	Approved
0.7456	Intermediate Similarity	NPD7640	Approved
0.7368	Intermediate Similarity	NPD7638	Approved
0.7355	Intermediate Similarity	NPD8297	Approved
0.7311	Intermediate Similarity	NPD6686	Approved
0.7227	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7507	Approved
0.7207	Intermediate Similarity	NPD6698	Approved
0.7207	Intermediate Similarity	NPD46	Approved
0.7188	Intermediate Similarity	NPD7604	Phase 2
0.7176	Intermediate Similarity	NPD7319	Approved
0.7167	Intermediate Similarity	NPD6899	Approved
0.7167	Intermediate Similarity	NPD6881	Approved
0.7154	Intermediate Similarity	NPD4632	Approved
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD7516	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.7131	Intermediate Similarity	NPD6649	Approved
0.7131	Intermediate Similarity	NPD8130	Phase 1
0.7131	Intermediate Similarity	NPD6650	Approved
0.7107	Intermediate Similarity	NPD6372	Approved
0.7107	Intermediate Similarity	NPD6373	Approved
0.7105	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6319	Approved
0.7083	Intermediate Similarity	NPD5697	Approved
0.7073	Intermediate Similarity	NPD6053	Discontinued
0.7063	Intermediate Similarity	NPD7328	Approved
0.7063	Intermediate Similarity	NPD7327	Approved
0.7049	Intermediate Similarity	NPD7290	Approved
0.7049	Intermediate Similarity	NPD7102	Approved
0.7049	Intermediate Similarity	NPD6883	Approved
0.7025	Intermediate Similarity	NPD7320	Approved
0.7	Intermediate Similarity	NPD7492	Approved
0.6992	Remote Similarity	NPD6847	Approved
0.6992	Remote Similarity	NPD6617	Approved
0.6992	Remote Similarity	NPD6869	Approved
0.6984	Remote Similarity	NPD6009	Approved
0.6983	Remote Similarity	NPD7902	Approved
0.697	Remote Similarity	NPD7736	Approved
0.6967	Remote Similarity	NPD6014	Approved
0.6967	Remote Similarity	NPD6012	Approved
0.6967	Remote Similarity	NPD6013	Approved
0.6953	Remote Similarity	NPD6054	Approved
0.6947	Remote Similarity	NPD6616	Approved
0.6942	Remote Similarity	NPD5701	Approved
0.6935	Remote Similarity	NPD6882	Approved
0.693	Remote Similarity	NPD6399	Phase 3
0.6903	Remote Similarity	NPD7838	Discovery
0.6899	Remote Similarity	NPD8379	Approved
0.6899	Remote Similarity	NPD5983	Phase 2
0.6899	Remote Similarity	NPD8033	Approved
0.6899	Remote Similarity	NPD8335	Approved
0.6899	Remote Similarity	NPD8296	Approved
0.6899	Remote Similarity	NPD8380	Approved
0.6899	Remote Similarity	NPD8378	Approved
0.6894	Remote Similarity	NPD7078	Approved
0.6894	Remote Similarity	NPD8293	Discontinued
0.6891	Remote Similarity	NPD5211	Phase 2
0.6891	Remote Similarity	NPD7632	Discontinued
0.6885	Remote Similarity	NPD6011	Approved
0.687	Remote Similarity	NPD7748	Approved
0.6846	Remote Similarity	NPD6370	Approved
0.6829	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD8294	Approved
0.6822	Remote Similarity	NPD6059	Approved
0.6822	Remote Similarity	NPD8377	Approved
0.6818	Remote Similarity	NPD6336	Discontinued
0.6814	Remote Similarity	NPD1695	Approved
0.6794	Remote Similarity	NPD8328	Phase 3
0.678	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD5141	Approved
0.6769	Remote Similarity	NPD8517	Approved
0.6769	Remote Similarity	NPD8515	Approved
0.6769	Remote Similarity	NPD8516	Approved
0.6769	Remote Similarity	NPD6015	Approved
0.6769	Remote Similarity	NPD6921	Approved
0.6769	Remote Similarity	NPD8513	Phase 3
0.6769	Remote Similarity	NPD6016	Approved
0.6757	Remote Similarity	NPD1694	Approved
0.6754	Remote Similarity	NPD5785	Approved
0.6746	Remote Similarity	NPD8133	Approved
0.6724	Remote Similarity	NPD7900	Approved
0.6724	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5286	Approved
0.6723	Remote Similarity	NPD4696	Approved
0.6723	Remote Similarity	NPD5285	Approved
0.672	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD5988	Approved
0.6696	Remote Similarity	NPD7515	Phase 2
0.6696	Remote Similarity	NPD7983	Approved
0.6696	Remote Similarity	NPD6079	Approved
0.6695	Remote Similarity	NPD6083	Phase 2
0.6695	Remote Similarity	NPD6084	Phase 2
0.6695	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6412	Phase 2
0.6641	Remote Similarity	NPD6274	Approved
0.6641	Remote Similarity	NPD7503	Approved
0.664	Remote Similarity	NPD4634	Approved
0.6638	Remote Similarity	NPD5779	Approved
0.6638	Remote Similarity	NPD5778	Approved
0.6636	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD7100	Approved
0.6615	Remote Similarity	NPD7101	Approved
0.6612	Remote Similarity	NPD5224	Approved
0.6612	Remote Similarity	NPD5226	Approved
0.6612	Remote Similarity	NPD5225	Approved
0.6612	Remote Similarity	NPD4633	Approved
0.6607	Remote Similarity	NPD1696	Phase 3
0.6607	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4700	Approved
0.6581	Remote Similarity	NPD5282	Discontinued
0.6569	Remote Similarity	NPD7260	Phase 2
0.6557	Remote Similarity	NPD5174	Approved
0.6557	Remote Similarity	NPD5175	Approved
0.6552	Remote Similarity	NPD8035	Phase 2
0.6552	Remote Similarity	NPD7637	Suspended
0.6552	Remote Similarity	NPD8034	Phase 2
0.6549	Remote Similarity	NPD3618	Phase 1
0.6538	Remote Similarity	NPD6335	Approved
0.6529	Remote Similarity	NPD5223	Approved
0.6525	Remote Similarity	NPD5695	Phase 3
0.6519	Remote Similarity	NPD8074	Phase 3
0.65	Remote Similarity	NPD5696	Approved
0.6496	Remote Similarity	NPD4202	Approved
0.6491	Remote Similarity	NPD7524	Approved
0.6471	Remote Similarity	NPD5222	Approved
0.6471	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4697	Phase 3
0.6471	Remote Similarity	NPD5221	Approved
0.6462	Remote Similarity	NPD6317	Approved
0.6462	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD5173	Approved
0.6412	Remote Similarity	NPD6313	Approved
0.6412	Remote Similarity	NPD6314	Approved
0.6391	Remote Similarity	NPD6909	Approved
0.6391	Remote Similarity	NPD6908	Approved
0.6391	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD6868	Approved
0.6372	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD4786	Approved
0.635	Remote Similarity	NPD6033	Approved
0.6349	Remote Similarity	NPD4729	Approved
0.6349	Remote Similarity	NPD4730	Approved
0.6349	Remote Similarity	NPD5128	Approved
0.6348	Remote Similarity	NPD3573	Approved
0.632	Remote Similarity	NPD4767	Approved
0.632	Remote Similarity	NPD4768	Approved
0.6316	Remote Similarity	NPD5363	Approved
0.6303	Remote Similarity	NPD6001	Approved
0.6293	Remote Similarity	NPD6672	Approved
0.6293	Remote Similarity	NPD5737	Approved
0.629	Remote Similarity	NPD4754	Approved
0.6286	Remote Similarity	NPD6845	Suspended
0.6283	Remote Similarity	NPD5362	Discontinued
0.6283	Remote Similarity	NPD7154	Phase 3
0.6283	Remote Similarity	NPD6695	Phase 3
0.6273	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5693	Phase 1
0.6271	Remote Similarity	NPD5281	Approved
0.6271	Remote Similarity	NPD5284	Approved
0.6271	Remote Similarity	NPD6411	Approved
0.6261	Remote Similarity	NPD7146	Approved
0.6261	Remote Similarity	NPD7334	Approved
0.6261	Remote Similarity	NPD6684	Approved
0.6261	Remote Similarity	NPD5330	Approved
0.6261	Remote Similarity	NPD7521	Approved
0.6261	Remote Similarity	NPD6409	Approved
0.626	Remote Similarity	NPD1700	Approved
0.625	Remote Similarity	NPD5251	Approved
0.625	Remote Similarity	NPD5250	Approved
0.625	Remote Similarity	NPD4629	Approved
0.625	Remote Similarity	NPD5210	Approved
0.625	Remote Similarity	NPD5247	Approved
0.625	Remote Similarity	NPD5248	Approved
0.625	Remote Similarity	NPD5249	Phase 3
0.6239	Remote Similarity	NPD4753	Phase 2
0.6207	Remote Similarity	NPD7750	Discontinued
0.6202	Remote Similarity	NPD5217	Approved
0.6202	Remote Similarity	NPD5216	Approved
0.6202	Remote Similarity	NPD5215	Approved
0.6195	Remote Similarity	NPD3667	Approved
0.6195	Remote Similarity	NPD5209	Approved
0.6186	Remote Similarity	NPD3168	Discontinued
0.6176	Remote Similarity	NPD6067	Discontinued
0.6174	Remote Similarity	NPD7520	Clinical (unspecified phase)

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