NPASS Compound

Structure

CID157252 OpenBabel06191715522D 36 39 0 0 1 0 0 0 0 0999 V2000 2.5305 4.5384 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 0.8136 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 2.5454 3.5385 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 0.7541 -2.4778 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 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 0.8884 -1.4869 0.0000 C 0 0 1 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 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 3.9921 -2.2764 0.0000 C 0 0 0 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 2.9921 -2.2764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7468 -0.9740 0.0000 C 0 0 1 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 2.2232 -2.9158 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 14 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 25 1 0 0 0 0 7 25 1 0 0 0 0 8 14 2 0 0 0 0 9 20 1 0 0 0 0 10 15 2 0 0 0 0 10 19 1 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 12 17 1 0 0 0 0 12 26 1 0 0 0 0 13 17 1 0 0 0 0 13 29 1 0 0 0 0 14 24 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 16 27 1 1 0 0 0 18 21 1 0 0 0 0 18 27 1 1 0 0 0 19 26 1 6 0 0 0 19 27 1 0 0 0 0 20 30 2 0 0 0 0 20 36 1 0 0 0 0 21 25 1 0 0 0 0 21 28 1 6 0 0 0 22 26 1 0 0 0 0 22 31 2 0 0 0 0 23 28 1 6 0 0 0 23 35 1 0 0 0 0 24 32 2 0 0 0 0 24 35 1 0 0 0 0 25 28 1 0 0 0 0 26 33 1 6 0 0 0 27 34 1 1 0 0 0 28 36 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.26
Volume:	513.121
LogP:	3.168
LogD:	1.872
LogS:	-4.184
# Rotatable Bonds:	7
TPSA:	130.36
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.297
Synthetic Accessibility Score:	5.239
Fsp3:	0.679
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.848
MDCK Permeability:	1.63121621881146e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.08
Human Intestinal Absorption (HIA):	0.312
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.547

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.441
Plasma Protein Binding (PPB):	62.53017044067383%
Volume Distribution (VD):	1.223
Pgp-substrate:	25.059711456298828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.237
CYP2C19-substrate:	0.549
CYP2C9-inhibitor:	0.339
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.061
CYP3A4-inhibitor:	0.675
CYP3A4-substrate:	0.299

ADMET: Excretion

Clearance (CL):	3.571
Half-life (T1/2):	0.55

ADMET: Toxicity

hERG Blockers:	0.457
Human Hepatotoxicity (H-HT):	0.942
Drug-inuced Liver Injury (DILI):	0.262
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.898
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.778
Carcinogencity:	0.104
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC157252

Natural Product ID:	NPC157252
*Common Name:**	WZPQMMCMYVTCRV-IFFRIBCBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WZPQMMCMYVTCRV-IFFRIBCBSA-N
Standard InCHI:	InChI=1S/C28H38O8/c1-8-14(3)24(32)35-23-16(5)27(34)18(21-25(6,7)28(21,23)36-20(30)9-2)11-17(13-29)12-26(33)19(27)10-15(4)22(26)31/h8,10-11,16,18-19,21,23,29,33-34H,9,12-13H2,1-7H3/b14-8+/t16-,18+,19-,21-,23-,26-,27-,28-/m1/s1
SMILES:	CCC(=O)O[C@@]12[C@H](OC(=O)/C(=C/C)/C)[C@@H](C)[C@]3([C@H]([C@@H]1C2(C)C)C=C(CO)C[C@]1([C@H]3C=C(C1=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375794
PubChem CID:	73348804
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 [CHEMONTID:0002906] Phorbol esters

*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	>	10200.0	nM	PMID[551604]

☑ 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 NPC157252 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	253
0.1-0.2	1496
0.2-0.3	4290
0.3-0.4	6872
0.4-0.5	13727
0.5-0.6	8371
0.6-0.7	5993
0.7-0.8	1481
0.8-0.85	92
0.85-0.9	23
0.9-0.95	55
0.95-1	44

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC145182
1.0	High Similarity	NPC471126
1.0	High Similarity	NPC471128
0.991	High Similarity	NPC52839
0.9818	High Similarity	NPC471125
0.9818	High Similarity	NPC472758
0.9818	High Similarity	NPC472397
0.9818	High Similarity	NPC171905
0.9735	High Similarity	NPC472399
0.973	High Similarity	NPC22628
0.973	High Similarity	NPC5989
0.973	High Similarity	NPC471108
0.973	High Similarity	NPC255081
0.973	High Similarity	NPC5991
0.973	High Similarity	NPC275696
0.9649	High Similarity	NPC145238
0.9646	High Similarity	NPC162009
0.9646	High Similarity	NPC257017
0.9636	High Similarity	NPC154363
0.9636	High Similarity	NPC471127
0.9636	High Similarity	NPC234858
0.9558	High Similarity	NPC472401
0.955	High Similarity	NPC156252
0.955	High Similarity	NPC10721
0.9545	High Similarity	NPC474872
0.9474	High Similarity	NPC19464
0.9455	High Similarity	NPC472757
0.9455	High Similarity	NPC71889
0.9381	High Similarity	NPC236918
0.9381	High Similarity	NPC156745
0.9369	High Similarity	NPC472400
0.9364	High Similarity	NPC475391
0.9298	High Similarity	NPC329080
0.9298	High Similarity	NPC475885
0.9298	High Similarity	NPC472759
0.9298	High Similarity	NPC185876
0.9298	High Similarity	NPC19336
0.9292	High Similarity	NPC146280
0.9292	High Similarity	NPC124676
0.9279	High Similarity	NPC474937
0.9273	High Similarity	NPC96739
0.9273	High Similarity	NPC474871
0.9273	High Similarity	NPC174471
0.9273	High Similarity	NPC475937
0.9273	High Similarity	NPC260786
0.9273	High Similarity	NPC158523
0.9237	High Similarity	NPC270109
0.9211	High Similarity	NPC180640
0.9189	High Similarity	NPC17138
0.9189	High Similarity	NPC215643
0.9189	High Similarity	NPC89227
0.9189	High Similarity	NPC265499
0.9189	High Similarity	NPC101825
0.9189	High Similarity	NPC170212
0.9189	High Similarity	NPC151216
0.9189	High Similarity	NPC221511
0.9182	High Similarity	NPC153036
0.9123	High Similarity	NPC472760
0.9068	High Similarity	NPC222307
0.9035	High Similarity	NPC153651
0.8983	High Similarity	NPC473919
0.8983	High Similarity	NPC473709
0.8919	High Similarity	NPC163004
0.8898	High Similarity	NPC473802
0.8833	High Similarity	NPC471940
0.8772	High Similarity	NPC477091
0.876	High Similarity	NPC236999
0.875	High Similarity	NPC471939
0.8718	High Similarity	NPC472667
0.8584	High Similarity	NPC273433
0.8571	High Similarity	NPC243902
0.8487	Intermediate Similarity	NPC143755
0.848	Intermediate Similarity	NPC476111
0.8417	Intermediate Similarity	NPC310511
0.84	Intermediate Similarity	NPC475139
0.84	Intermediate Similarity	NPC180902
0.8347	Intermediate Similarity	NPC222688
0.8306	Intermediate Similarity	NPC470850
0.8305	Intermediate Similarity	NPC470793
0.8305	Intermediate Similarity	NPC179626
0.8293	Intermediate Similarity	NPC217901
0.8291	Intermediate Similarity	NPC477126
0.8268	Intermediate Similarity	NPC182266
0.8268	Intermediate Similarity	NPC100017
0.8268	Intermediate Similarity	NPC475500
0.8268	Intermediate Similarity	NPC475154
0.8268	Intermediate Similarity	NPC471137
0.8268	Intermediate Similarity	NPC473548
0.8268	Intermediate Similarity	NPC471136
0.8268	Intermediate Similarity	NPC476823
0.8268	Intermediate Similarity	NPC223356
0.8254	Intermediate Similarity	NPC90814
0.8254	Intermediate Similarity	NPC189393
0.8246	Intermediate Similarity	NPC187435
0.8246	Intermediate Similarity	NPC143609
0.8246	Intermediate Similarity	NPC67321
0.824	Intermediate Similarity	NPC162495
0.824	Intermediate Similarity	NPC470851
0.824	Intermediate Similarity	NPC104382
0.8226	Intermediate Similarity	NPC168849
0.8226	Intermediate Similarity	NPC475273
0.8205	Intermediate Similarity	NPC317687
0.819	Intermediate Similarity	NPC477103
0.819	Intermediate Similarity	NPC5103
0.819	Intermediate Similarity	NPC257240
0.8189	Intermediate Similarity	NPC469673
0.8182	Intermediate Similarity	NPC4548
0.8182	Intermediate Similarity	NPC472004
0.8175	Intermediate Similarity	NPC475314
0.8175	Intermediate Similarity	NPC196921
0.8175	Intermediate Similarity	NPC220757
0.8175	Intermediate Similarity	NPC477189
0.8175	Intermediate Similarity	NPC251564
0.8175	Intermediate Similarity	NPC475606
0.8174	Intermediate Similarity	NPC476479
0.8167	Intermediate Similarity	NPC251310
0.8158	Intermediate Similarity	NPC111952
0.8145	Intermediate Similarity	NPC293112
0.8145	Intermediate Similarity	NPC15095
0.814	Intermediate Similarity	NPC68282
0.8136	Intermediate Similarity	NPC469454
0.8136	Intermediate Similarity	NPC469463
0.8136	Intermediate Similarity	NPC469496
0.813	Intermediate Similarity	NPC67251
0.812	Intermediate Similarity	NPC317107
0.812	Intermediate Similarity	NPC474846
0.812	Intermediate Similarity	NPC475668
0.812	Intermediate Similarity	NPC473921
0.812	Intermediate Similarity	NPC469655
0.812	Intermediate Similarity	NPC469656
0.812	Intermediate Similarity	NPC475480
0.811	Intermediate Similarity	NPC34963
0.811	Intermediate Similarity	NPC473485
0.811	Intermediate Similarity	NPC474508
0.8103	Intermediate Similarity	NPC471934
0.8103	Intermediate Similarity	NPC42662
0.8103	Intermediate Similarity	NPC477102
0.8099	Intermediate Similarity	NPC476529
0.8099	Intermediate Similarity	NPC475775
0.8099	Intermediate Similarity	NPC469380
0.8099	Intermediate Similarity	NPC475041
0.8095	Intermediate Similarity	NPC175186
0.8095	Intermediate Similarity	NPC35109
0.8095	Intermediate Similarity	NPC231529
0.8087	Intermediate Similarity	NPC474716
0.8083	Intermediate Similarity	NPC469684
0.8083	Intermediate Similarity	NPC296822
0.8083	Intermediate Similarity	NPC473590
0.8067	Intermediate Similarity	NPC178289
0.8067	Intermediate Similarity	NPC473798
0.8065	Intermediate Similarity	NPC476729
0.8065	Intermediate Similarity	NPC470922
0.8065	Intermediate Similarity	NPC24651
0.8065	Intermediate Similarity	NPC172154
0.8065	Intermediate Similarity	NPC81736
0.8053	Intermediate Similarity	NPC476081
0.8051	Intermediate Similarity	NPC474516
0.8051	Intermediate Similarity	NPC472002
0.8051	Intermediate Similarity	NPC473877
0.8049	Intermediate Similarity	NPC23786
0.8049	Intermediate Similarity	NPC269642
0.8049	Intermediate Similarity	NPC470265
0.8047	Intermediate Similarity	NPC58029
0.8034	Intermediate Similarity	NPC475563
0.8034	Intermediate Similarity	NPC253906
0.8034	Intermediate Similarity	NPC475134
0.8033	Intermediate Similarity	NPC107338
0.8033	Intermediate Similarity	NPC109607
0.8031	Intermediate Similarity	NPC241935
0.8031	Intermediate Similarity	NPC279478
0.8031	Intermediate Similarity	NPC471170
0.8031	Intermediate Similarity	NPC476855
0.8017	Intermediate Similarity	NPC306265
0.8017	Intermediate Similarity	NPC311554
0.8017	Intermediate Similarity	NPC469916
0.8017	Intermediate Similarity	NPC257457
0.8017	Intermediate Similarity	NPC472439
0.8017	Intermediate Similarity	NPC322903
0.8016	Intermediate Similarity	NPC476859
0.8	Intermediate Similarity	NPC96312
0.8	Intermediate Similarity	NPC251236
0.8	Intermediate Similarity	NPC476710
0.8	Intermediate Similarity	NPC470973
0.8	Intermediate Similarity	NPC328374
0.8	Intermediate Similarity	NPC40632
0.8	Intermediate Similarity	NPC474734
0.8	Intermediate Similarity	NPC476711
0.8	Intermediate Similarity	NPC471816
0.8	Intermediate Similarity	NPC473635
0.8	Intermediate Similarity	NPC270478
0.8	Intermediate Similarity	NPC474333
0.8	Intermediate Similarity	NPC148458
0.8	Intermediate Similarity	NPC176840
0.7984	Intermediate Similarity	NPC473979
0.7984	Intermediate Similarity	NPC469352
0.7984	Intermediate Similarity	NPC11895
0.7984	Intermediate Similarity	NPC105926
0.7984	Intermediate Similarity	NPC91693
0.7984	Intermediate Similarity	NPC18945
0.7984	Intermediate Similarity	NPC265557

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 NPC157252 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	1901
0.2-0.3	3597
0.3-0.4	2165
0.4-0.5	831
0.5-0.6	258
0.6-0.7	161
0.7-0.8	14
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
0.819	Intermediate Similarity	NPD6371	Approved
0.7731	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD5344	Discontinued
0.7647	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD7115	Discovery
0.7603	Intermediate Similarity	NPD8297	Approved
0.7563	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD6650	Approved
0.7521	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD6372	Approved
0.7479	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6319	Approved
0.7422	Intermediate Similarity	NPD7604	Phase 2
0.7417	Intermediate Similarity	NPD6881	Approved
0.7417	Intermediate Similarity	NPD6899	Approved
0.7414	Intermediate Similarity	NPD7640	Approved
0.7414	Intermediate Similarity	NPD7639	Approved
0.7414	Intermediate Similarity	NPD6648	Approved
0.7398	Intermediate Similarity	NPD4632	Approved
0.7395	Intermediate Similarity	NPD7128	Approved
0.7395	Intermediate Similarity	NPD6675	Approved
0.7395	Intermediate Similarity	NPD6402	Approved
0.7395	Intermediate Similarity	NPD5739	Approved
0.7333	Intermediate Similarity	NPD5697	Approved
0.7328	Intermediate Similarity	NPD4225	Approved
0.7328	Intermediate Similarity	NPD7638	Approved
0.7317	Intermediate Similarity	NPD6882	Approved
0.7308	Intermediate Similarity	NPD7507	Approved
0.7295	Intermediate Similarity	NPD7290	Approved
0.7295	Intermediate Similarity	NPD7102	Approved
0.7295	Intermediate Similarity	NPD6883	Approved
0.7273	Intermediate Similarity	NPD6686	Approved
0.7273	Intermediate Similarity	NPD7319	Approved
0.7273	Intermediate Similarity	NPD7320	Approved
0.7244	Intermediate Similarity	NPD7516	Approved
0.7236	Intermediate Similarity	NPD6617	Approved
0.7236	Intermediate Similarity	NPD6869	Approved
0.7236	Intermediate Similarity	NPD6847	Approved
0.7236	Intermediate Similarity	NPD8130	Phase 1
0.7231	Intermediate Similarity	NPD7492	Approved
0.7222	Intermediate Similarity	NPD6009	Approved
0.7213	Intermediate Similarity	NPD6012	Approved
0.7213	Intermediate Similarity	NPD6013	Approved
0.7213	Intermediate Similarity	NPD6014	Approved
0.719	Intermediate Similarity	NPD5701	Approved
0.7188	Intermediate Similarity	NPD6054	Approved
0.7176	Intermediate Similarity	NPD6616	Approved
0.7168	Intermediate Similarity	NPD6698	Approved
0.7168	Intermediate Similarity	NPD46	Approved
0.7165	Intermediate Similarity	NPD7327	Approved
0.7165	Intermediate Similarity	NPD7328	Approved
0.7143	Intermediate Similarity	NPD5211	Phase 2
0.7132	Intermediate Similarity	NPD5983	Phase 2
0.7131	Intermediate Similarity	NPD6011	Approved
0.7121	Intermediate Similarity	NPD7078	Approved
0.7107	Intermediate Similarity	NPD6008	Approved
0.7077	Intermediate Similarity	NPD6370	Approved
0.7068	Intermediate Similarity	NPD7736	Approved
0.7054	Intermediate Similarity	NPD6059	Approved
0.7045	Intermediate Similarity	NPD6336	Discontinued
0.704	Intermediate Similarity	NPD6053	Discontinued
0.7025	Intermediate Similarity	NPD5141	Approved
0.7	Intermediate Similarity	NPD6015	Approved
0.7	Intermediate Similarity	NPD6016	Approved
0.7	Intermediate Similarity	NPD6921	Approved
0.6992	Remote Similarity	NPD8293	Discontinued
0.6975	Remote Similarity	NPD5286	Approved
0.6975	Remote Similarity	NPD4696	Approved
0.6975	Remote Similarity	NPD5285	Approved
0.696	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6084	Phase 2
0.6949	Remote Similarity	NPD6083	Phase 2
0.6949	Remote Similarity	NPD4755	Approved
0.6947	Remote Similarity	NPD5988	Approved
0.6923	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD8328	Phase 3
0.688	Remote Similarity	NPD4634	Approved
0.6875	Remote Similarity	NPD6274	Approved
0.687	Remote Similarity	NPD8379	Approved
0.687	Remote Similarity	NPD8296	Approved
0.687	Remote Similarity	NPD8033	Approved
0.687	Remote Similarity	NPD8378	Approved
0.687	Remote Similarity	NPD8380	Approved
0.687	Remote Similarity	NPD8335	Approved
0.686	Remote Similarity	NPD5225	Approved
0.686	Remote Similarity	NPD4633	Approved
0.686	Remote Similarity	NPD5226	Approved
0.686	Remote Similarity	NPD5224	Approved
0.686	Remote Similarity	NPD7632	Discontinued
0.6846	Remote Similarity	NPD7100	Approved
0.6846	Remote Similarity	NPD7101	Approved
0.6833	Remote Similarity	NPD4700	Approved
0.6803	Remote Similarity	NPD5175	Approved
0.6803	Remote Similarity	NPD5174	Approved
0.6794	Remote Similarity	NPD8377	Approved
0.6794	Remote Similarity	NPD8294	Approved
0.6788	Remote Similarity	NPD7260	Phase 2
0.6783	Remote Similarity	NPD1695	Approved
0.678	Remote Similarity	NPD5695	Phase 3
0.6777	Remote Similarity	NPD5223	Approved
0.6769	Remote Similarity	NPD6335	Approved
0.6752	Remote Similarity	NPD6399	Phase 3
0.675	Remote Similarity	NPD5696	Approved
0.6742	Remote Similarity	NPD7503	Approved
0.6726	Remote Similarity	NPD1696	Phase 3
0.6724	Remote Similarity	NPD7838	Discovery
0.6724	Remote Similarity	NPD5785	Approved
0.672	Remote Similarity	NPD4730	Approved
0.672	Remote Similarity	NPD4729	Approved
0.6719	Remote Similarity	NPD8133	Approved
0.6695	Remote Similarity	NPD5282	Discontinued
0.6694	Remote Similarity	NPD4767	Approved
0.6694	Remote Similarity	NPD4768	Approved
0.6693	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6313	Approved
0.6641	Remote Similarity	NPD6314	Approved
0.664	Remote Similarity	NPD6412	Phase 2
0.6639	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD8517	Approved
0.6617	Remote Similarity	NPD6909	Approved
0.6617	Remote Similarity	NPD8515	Approved
0.6617	Remote Similarity	NPD8516	Approved
0.6617	Remote Similarity	NPD6908	Approved
0.6617	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD8513	Phase 3
0.6614	Remote Similarity	NPD5249	Phase 3
0.6614	Remote Similarity	NPD5247	Approved
0.6614	Remote Similarity	NPD5251	Approved
0.6614	Remote Similarity	NPD5250	Approved
0.6614	Remote Similarity	NPD5248	Approved
0.6612	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD5128	Approved
0.6583	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD5221	Approved
0.6583	Remote Similarity	NPD5222	Approved
0.6583	Remote Similarity	NPD4697	Phase 3
0.6579	Remote Similarity	NPD1694	Approved
0.6569	Remote Similarity	NPD6033	Approved
0.6565	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7748	Approved
0.6532	Remote Similarity	NPD4754	Approved
0.6529	Remote Similarity	NPD5173	Approved
0.6525	Remote Similarity	NPD6079	Approved
0.6525	Remote Similarity	NPD5693	Phase 1
0.6525	Remote Similarity	NPD7515	Phase 2
0.6525	Remote Similarity	NPD7983	Approved
0.6504	Remote Similarity	NPD1700	Approved
0.65	Remote Similarity	NPD6845	Suspended
0.65	Remote Similarity	NPD5210	Approved
0.65	Remote Similarity	NPD4629	Approved
0.6496	Remote Similarity	NPD4753	Phase 2
0.6496	Remote Similarity	NPD5328	Approved
0.6489	Remote Similarity	NPD6868	Approved
0.6471	Remote Similarity	NPD5779	Approved
0.6471	Remote Similarity	NPD4202	Approved
0.6471	Remote Similarity	NPD5778	Approved
0.646	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD5215	Approved
0.6434	Remote Similarity	NPD5216	Approved
0.6434	Remote Similarity	NPD5217	Approved
0.6417	Remote Similarity	NPD7900	Approved
0.6417	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5737	Approved
0.641	Remote Similarity	NPD6672	Approved
0.6387	Remote Similarity	NPD7637	Suspended
0.6379	Remote Similarity	NPD3618	Phase 1
0.6377	Remote Similarity	NPD8074	Phase 3
0.6357	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD5135	Approved
0.6357	Remote Similarity	NPD5169	Approved
0.6356	Remote Similarity	NPD6673	Approved
0.6356	Remote Similarity	NPD6080	Approved
0.6356	Remote Similarity	NPD6904	Approved
0.6325	Remote Similarity	NPD7524	Approved
0.6308	Remote Similarity	NPD5127	Approved
0.6293	Remote Similarity	NPD5363	Approved
0.6281	Remote Similarity	NPD6001	Approved
0.6261	Remote Similarity	NPD6110	Phase 1
0.6261	Remote Similarity	NPD7154	Phase 3
0.6261	Remote Similarity	NPD5362	Discontinued
0.625	Remote Similarity	NPD5284	Approved
0.625	Remote Similarity	NPD8035	Phase 2
0.625	Remote Similarity	NPD8034	Phase 2
0.625	Remote Similarity	NPD6050	Approved
0.625	Remote Similarity	NPD5281	Approved
0.6239	Remote Similarity	NPD6684	Approved
0.6239	Remote Similarity	NPD7521	Approved
0.6239	Remote Similarity	NPD7334	Approved
0.6239	Remote Similarity	NPD5330	Approved
0.6239	Remote Similarity	NPD7146	Approved
0.6239	Remote Similarity	NPD6409	Approved
0.6207	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4786	Approved
0.6186	Remote Similarity	NPD3573	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