NPASS Compound

Structure

NPC472148 OpenBabel07101719252D 35 40 0 0 1 0 0 0 0 0999 V2000 -2.8873 -3.1865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9410 -3.5097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0841 2.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0841 2.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9605 -0.9158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1528 0.5842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4737 -1.1021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3369 1.1643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7133 0.8043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7922 -1.7755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4734 0.1731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4690 -0.8292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1754 0.0129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3369 -0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5841 -0.2759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1531 -2.3353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2077 0.0842 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9605 0.8043 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3369 -0.2759 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8299 -1.3890 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7133 -1.3560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2077 0.8043 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9749 0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1342 -2.5286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5841 1.1643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9605 0.0842 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7133 0.0842 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0896 -0.2759 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4878 -0.6359 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0896 -0.9960 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0738 -0.4158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7133 -2.3560 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0738 1.3043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3680 1.1420 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 24 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 6 27 1 0 0 0 0 7 28 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 27 1 0 0 0 0 10 12 1 0 0 0 0 10 24 1 0 0 0 0 11 13 1 0 0 0 0 11 28 1 0 0 0 0 13 29 1 0 0 0 0 14 19 1 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 15 26 1 0 0 0 0 16 20 1 0 0 0 0 16 24 1 0 0 0 0 17 22 1 0 0 0 0 17 31 1 6 0 0 0 18 25 1 0 0 0 0 18 26 1 1 0 0 0 19 26 1 1 0 0 0 19 27 1 0 0 0 0 20 29 1 6 0 0 0 20 30 1 0 0 0 0 21 32 2 0 0 0 0 22 25 1 0 0 0 0 22 33 1 6 0 0 0 23 29 1 0 0 0 0 23 34 2 0 0 0 0 23 35 1 0 0 0 0 26 5 1 1 0 0 0 27 28 1 6 0 0 0 28 30 1 1 0 0 0 29 12 1 1 0 0 0 30 21 1 1 0 0 0 30 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	514.775
LogP:	4.642
LogD:	4.462
LogS:	-5.138
# Rotatable Bonds:	0
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.468
Synthetic Accessibility Score:	6.403
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.29
MDCK Permeability:	2.4511449737474322e-05
Pgp-inhibitor:	0.925
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.192
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.465
Plasma Protein Binding (PPB):	87.69391632080078%
Volume Distribution (VD):	0.866
Pgp-substrate:	7.140325546264648%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.536
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.901
CYP2C9-inhibitor:	0.152
CYP2C9-substrate:	0.093
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.069
CYP3A4-inhibitor:	0.603
CYP3A4-substrate:	0.526

ADMET: Excretion

Clearance (CL):	6.635
Half-life (T1/2):	0.162

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.314
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.964
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.095
Carcinogencity:	0.123
Eye Corrosion:	0.007
Eye Irritation:	0.037
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC472148

Natural Product ID:	NPC472148
*Common Name:**	CWGOYIQCGRKVNH-AWJYMUORSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CWGOYIQCGRKVNH-AWJYMUORSA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-24(2)10-12-29-13-11-28(7)27(6)9-8-18-25(3,4)22(33)17(31)15-26(18,5)19(27)14-21(32)30(28,20(29)16-24)35-23(29)34/h17-20,22,31,33H,8-16H2,1-7H3/t17-,18+,19-,20-,22-,26+,27-,28+,29+,30-/m1/s1
SMILES:	CC1(CCC23CCC4(C5(CCC6C(C(C(CC6(C5CC(=O)C4(C2C1)OC3=O)C)O)O)(C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342055
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO14026.1	Vitex negundo var. cannabifolia	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25245917]
NPO14026.1	Vitex negundo var. cannabifolia	Varieties	Lamiaceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	<	70.0	%	PMID[518035]

☑ 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 NPC472148 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	446
0.1-0.2	3411
0.2-0.3	10618
0.3-0.4	13107
0.4-0.5	6182
0.5-0.6	4762
0.6-0.7	3413
0.7-0.8	696
0.8-0.85	47
0.85-0.9	10
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472147
0.9186	High Similarity	NPC62572
0.8889	High Similarity	NPC472146
0.8889	High Similarity	NPC185529
0.8851	High Similarity	NPC105895
0.8721	High Similarity	NPC280781
0.8721	High Similarity	NPC48756
0.8602	High Similarity	NPC247877
0.8602	High Similarity	NPC309127
0.8421	Intermediate Similarity	NPC163685
0.8372	Intermediate Similarity	NPC26029
0.8352	Intermediate Similarity	NPC470920
0.8333	Intermediate Similarity	NPC470632
0.8316	Intermediate Similarity	NPC82633
0.8295	Intermediate Similarity	NPC50658
0.828	Intermediate Similarity	NPC50443
0.828	Intermediate Similarity	NPC18536
0.8276	Intermediate Similarity	NPC73013
0.8261	Intermediate Similarity	NPC236459
0.8247	Intermediate Similarity	NPC472144
0.8242	Intermediate Similarity	NPC120395
0.8242	Intermediate Similarity	NPC248216
0.8229	Intermediate Similarity	NPC235109
0.8222	Intermediate Similarity	NPC25037
0.8222	Intermediate Similarity	NPC34984
0.8202	Intermediate Similarity	NPC30583
0.8202	Intermediate Similarity	NPC61107
0.8202	Intermediate Similarity	NPC289486
0.8161	Intermediate Similarity	NPC243594
0.8161	Intermediate Similarity	NPC31031
0.8161	Intermediate Similarity	NPC472608
0.8144	Intermediate Similarity	NPC472145
0.8144	Intermediate Similarity	NPC74466
0.809	Intermediate Similarity	NPC474870
0.809	Intermediate Similarity	NPC476071
0.809	Intermediate Similarity	NPC271572
0.8043	Intermediate Similarity	NPC92139
0.8023	Intermediate Similarity	NPC267753
0.8022	Intermediate Similarity	NPC473299
0.7979	Intermediate Similarity	NPC67653
0.7979	Intermediate Similarity	NPC471459
0.7961	Intermediate Similarity	NPC316930
0.7935	Intermediate Similarity	NPC477445
0.7931	Intermediate Similarity	NPC108840
0.7912	Intermediate Similarity	NPC269684
0.7907	Intermediate Similarity	NPC168511
0.7907	Intermediate Similarity	NPC130011
0.7907	Intermediate Similarity	NPC159325
0.7889	Intermediate Similarity	NPC58631
0.7885	Intermediate Similarity	NPC321661
0.7885	Intermediate Similarity	NPC320475
0.7857	Intermediate Similarity	NPC223169
0.7835	Intermediate Similarity	NPC206878
0.7826	Intermediate Similarity	NPC219535
0.7826	Intermediate Similarity	NPC474996
0.7826	Intermediate Similarity	NPC237938
0.7791	Intermediate Similarity	NPC68426
0.7791	Intermediate Similarity	NPC81759
0.7791	Intermediate Similarity	NPC282905
0.7791	Intermediate Similarity	NPC477229
0.7778	Intermediate Similarity	NPC261616
0.7742	Intermediate Similarity	NPC131350
0.7708	Intermediate Similarity	NPC477442
0.7708	Intermediate Similarity	NPC477444
0.7708	Intermediate Similarity	NPC477433
0.77	Intermediate Similarity	NPC474724
0.7692	Intermediate Similarity	NPC12933
0.7684	Intermediate Similarity	NPC473319
0.7684	Intermediate Similarity	NPC3032
0.7684	Intermediate Similarity	NPC131104
0.7684	Intermediate Similarity	NPC476435
0.767	Intermediate Similarity	NPC327093
0.7667	Intermediate Similarity	NPC320144
0.766	Intermediate Similarity	NPC80700
0.766	Intermediate Similarity	NPC83242
0.764	Intermediate Similarity	NPC112463
0.764	Intermediate Similarity	NPC307865
0.764	Intermediate Similarity	NPC143133
0.764	Intermediate Similarity	NPC23884
0.764	Intermediate Similarity	NPC298168
0.7634	Intermediate Similarity	NPC79308
0.7634	Intermediate Similarity	NPC477434
0.7624	Intermediate Similarity	NPC80417
0.7614	Intermediate Similarity	NPC179858
0.7609	Intermediate Similarity	NPC328007
0.7609	Intermediate Similarity	NPC121121
0.7604	Intermediate Similarity	NPC477443
0.7604	Intermediate Similarity	NPC477440
0.76	Intermediate Similarity	NPC470425
0.7586	Intermediate Similarity	NPC475230
0.7576	Intermediate Similarity	NPC470031
0.7573	Intermediate Similarity	NPC225238
0.7556	Intermediate Similarity	NPC185465
0.7551	Intermediate Similarity	NPC474379
0.7547	Intermediate Similarity	NPC154906
0.7528	Intermediate Similarity	NPC5767
0.7528	Intermediate Similarity	NPC4209
0.7528	Intermediate Similarity	NPC475742
0.7528	Intermediate Similarity	NPC471046
0.7526	Intermediate Similarity	NPC475211
0.7526	Intermediate Similarity	NPC88337
0.7526	Intermediate Similarity	NPC470114
0.7524	Intermediate Similarity	NPC203974
0.7523	Intermediate Similarity	NPC477465
0.75	Intermediate Similarity	NPC476379
0.75	Intermediate Similarity	NPC284865
0.75	Intermediate Similarity	NPC475785
0.75	Intermediate Similarity	NPC90676
0.7477	Intermediate Similarity	NPC470622
0.7476	Intermediate Similarity	NPC80640
0.7475	Intermediate Similarity	NPC470424
0.7474	Intermediate Similarity	NPC476727
0.7474	Intermediate Similarity	NPC472272
0.7474	Intermediate Similarity	NPC476726
0.7473	Intermediate Similarity	NPC472310
0.7473	Intermediate Similarity	NPC201276
0.7473	Intermediate Similarity	NPC80891
0.7471	Intermediate Similarity	NPC290058
0.7449	Intermediate Similarity	NPC216137
0.7447	Intermediate Similarity	NPC473336
0.7447	Intermediate Similarity	NPC471044
0.7444	Intermediate Similarity	NPC207010
0.7444	Intermediate Similarity	NPC317913
0.7444	Intermediate Similarity	NPC221420
0.7431	Intermediate Similarity	NPC97002
0.7429	Intermediate Similarity	NPC181357
0.7426	Intermediate Similarity	NPC259788
0.7426	Intermediate Similarity	NPC255589
0.7423	Intermediate Similarity	NPC11611
0.7423	Intermediate Similarity	NPC220498
0.7419	Intermediate Similarity	NPC317066
0.7416	Intermediate Similarity	NPC97534
0.7416	Intermediate Similarity	NPC212733
0.7416	Intermediate Similarity	NPC174964
0.7416	Intermediate Similarity	NPC472311
0.7416	Intermediate Similarity	NPC195155
0.74	Intermediate Similarity	NPC62407
0.74	Intermediate Similarity	NPC287354
0.7396	Intermediate Similarity	NPC239938
0.7391	Intermediate Similarity	NPC472853
0.7387	Intermediate Similarity	NPC470778
0.7387	Intermediate Similarity	NPC146432
0.7386	Intermediate Similarity	NPC109510
0.7383	Intermediate Similarity	NPC236753
0.7383	Intermediate Similarity	NPC228190
0.7379	Intermediate Similarity	NPC54909
0.7379	Intermediate Similarity	NPC233012
0.7374	Intermediate Similarity	NPC63118
0.7374	Intermediate Similarity	NPC136313
0.7374	Intermediate Similarity	NPC275809
0.7374	Intermediate Similarity	NPC74855
0.7374	Intermediate Similarity	NPC49776
0.7374	Intermediate Similarity	NPC307335
0.7374	Intermediate Similarity	NPC474436
0.7363	Intermediate Similarity	NPC199965
0.7363	Intermediate Similarity	NPC34046
0.7363	Intermediate Similarity	NPC324700
0.7363	Intermediate Similarity	NPC224802
0.7363	Intermediate Similarity	NPC476732
0.7363	Intermediate Similarity	NPC80089
0.7363	Intermediate Similarity	NPC171426
0.7358	Intermediate Similarity	NPC301666
0.7358	Intermediate Similarity	NPC126753
0.7347	Intermediate Similarity	NPC263977
0.7347	Intermediate Similarity	NPC49320
0.734	Intermediate Similarity	NPC327451
0.7333	Intermediate Similarity	NPC472486
0.7333	Intermediate Similarity	NPC267637
0.7333	Intermediate Similarity	NPC472487
0.7327	Intermediate Similarity	NPC476728
0.7327	Intermediate Similarity	NPC256227
0.7327	Intermediate Similarity	NPC230151
0.7327	Intermediate Similarity	NPC475765
0.7327	Intermediate Similarity	NPC158371
0.7327	Intermediate Similarity	NPC62516
0.7327	Intermediate Similarity	NPC259733
0.7327	Intermediate Similarity	NPC207922
0.7327	Intermediate Similarity	NPC104568
0.7327	Intermediate Similarity	NPC116683
0.7327	Intermediate Similarity	NPC157113
0.7326	Intermediate Similarity	NPC31187
0.7326	Intermediate Similarity	NPC100917
0.7326	Intermediate Similarity	NPC2568
0.7326	Intermediate Similarity	NPC281203
0.7326	Intermediate Similarity	NPC475893
0.7326	Intermediate Similarity	NPC469724
0.7326	Intermediate Similarity	NPC260319
0.7326	Intermediate Similarity	NPC180777
0.7326	Intermediate Similarity	NPC103647
0.732	Intermediate Similarity	NPC471221
0.732	Intermediate Similarity	NPC474719
0.7303	Intermediate Similarity	NPC280026
0.7303	Intermediate Similarity	NPC317212
0.7303	Intermediate Similarity	NPC254340
0.7303	Intermediate Similarity	NPC167702
0.7303	Intermediate Similarity	NPC74639
0.7303	Intermediate Similarity	NPC133922
0.7303	Intermediate Similarity	NPC55508
0.73	Intermediate Similarity	NPC303863
0.7297	Intermediate Similarity	NPC173686

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 NPC472148 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	469
0.1-0.2	3596
0.2-0.3	3441
0.3-0.4	1030
0.4-0.5	302
0.5-0.6	189
0.6-0.7	105
0.7-0.8	18
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
0.7528	Intermediate Similarity	NPD6117	Approved
0.7444	Intermediate Similarity	NPD6116	Phase 1
0.7363	Intermediate Similarity	NPD6118	Approved
0.7363	Intermediate Similarity	NPD6114	Approved
0.7363	Intermediate Similarity	NPD6697	Approved
0.7363	Intermediate Similarity	NPD6115	Approved
0.7303	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD8035	Phase 2
0.71	Intermediate Similarity	NPD8034	Phase 2
0.7079	Intermediate Similarity	NPD6081	Approved
0.7079	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3703	Phase 2
0.701	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4789	Approved
0.6961	Remote Similarity	NPD7748	Approved
0.6931	Remote Similarity	NPD7515	Phase 2
0.6923	Remote Similarity	NPD7902	Approved
0.6889	Remote Similarity	NPD5777	Approved
0.6848	Remote Similarity	NPD3702	Approved
0.6789	Remote Similarity	NPD6675	Approved
0.6789	Remote Similarity	NPD7128	Approved
0.6789	Remote Similarity	NPD6402	Approved
0.6789	Remote Similarity	NPD5739	Approved
0.6783	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4245	Approved
0.6778	Remote Similarity	NPD4244	Approved
0.6757	Remote Similarity	NPD6372	Approved
0.6757	Remote Similarity	NPD6373	Approved
0.6742	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5360	Phase 3
0.6705	Remote Similarity	NPD4224	Phase 2
0.6697	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3698	Phase 2
0.6667	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6637	Remote Similarity	NPD6649	Approved
0.6637	Remote Similarity	NPD6650	Approved
0.6635	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7900	Approved
0.6607	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD8328	Phase 3
0.6579	Remote Similarity	NPD8297	Approved
0.6577	Remote Similarity	NPD5697	Approved
0.6577	Remote Similarity	NPD5701	Approved
0.6574	Remote Similarity	NPD1700	Approved
0.6549	Remote Similarity	NPD6883	Approved
0.6549	Remote Similarity	NPD7102	Approved
0.6549	Remote Similarity	NPD7290	Approved
0.6542	Remote Similarity	NPD5696	Approved
0.6518	Remote Similarity	NPD6011	Approved
0.6491	Remote Similarity	NPD6617	Approved
0.6491	Remote Similarity	NPD6847	Approved
0.6491	Remote Similarity	NPD6869	Approved
0.6491	Remote Similarity	NPD8130	Phase 1
0.6491	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6013	Approved
0.646	Remote Similarity	NPD6014	Approved
0.646	Remote Similarity	NPD6012	Approved
0.6458	Remote Similarity	NPD3671	Phase 1
0.6449	Remote Similarity	NPD6084	Phase 2
0.6449	Remote Similarity	NPD6083	Phase 2
0.6435	Remote Similarity	NPD6882	Approved
0.6404	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6399	Phase 3
0.6344	Remote Similarity	NPD4758	Discontinued
0.6289	Remote Similarity	NPD5364	Discontinued
0.6281	Remote Similarity	NPD6921	Approved
0.624	Remote Similarity	NPD7736	Approved
0.6239	Remote Similarity	NPD4632	Approved
0.6239	Remote Similarity	NPD8133	Approved
0.6218	Remote Similarity	NPD7115	Discovery
0.6204	Remote Similarity	NPD4697	Phase 3
0.6198	Remote Similarity	NPD6319	Approved
0.6195	Remote Similarity	NPD6920	Discontinued
0.6174	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD6335	Approved
0.6154	Remote Similarity	NPD5737	Approved
0.6154	Remote Similarity	NPD6672	Approved
0.6147	Remote Similarity	NPD4755	Approved
0.6134	Remote Similarity	NPD6274	Approved
0.6134	Remote Similarity	NPD6868	Approved
0.6129	Remote Similarity	NPD7492	Approved
0.6117	Remote Similarity	NPD3618	Phase 1
0.6116	Remote Similarity	NPD7100	Approved
0.6116	Remote Similarity	NPD7101	Approved
0.6111	Remote Similarity	NPD7909	Approved
0.6111	Remote Similarity	NPD5695	Phase 3
0.6095	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5328	Approved
0.6091	Remote Similarity	NPD7638	Approved
0.6083	Remote Similarity	NPD6009	Approved
0.6083	Remote Similarity	NPD6317	Approved
0.608	Remote Similarity	NPD6616	Approved
0.6066	Remote Similarity	NPD6054	Approved
0.6066	Remote Similarity	NPD6059	Approved
0.6055	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD5222	Approved
0.6055	Remote Similarity	NPD5221	Approved
0.6048	Remote Similarity	NPD7604	Phase 2
0.6036	Remote Similarity	NPD7639	Approved
0.6036	Remote Similarity	NPD7640	Approved
0.6036	Remote Similarity	NPD4696	Approved
0.6036	Remote Similarity	NPD5285	Approved
0.6036	Remote Similarity	NPD5286	Approved
0.6036	Remote Similarity	NPD8418	Phase 2
0.6036	Remote Similarity	NPD4700	Approved
0.6033	Remote Similarity	NPD6314	Approved
0.6033	Remote Similarity	NPD6313	Approved
0.6032	Remote Similarity	NPD7078	Approved
0.6032	Remote Similarity	NPD8293	Discontinued
0.6016	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6909	Approved
0.6016	Remote Similarity	NPD6908	Approved
0.6016	Remote Similarity	NPD5983	Phase 2
0.6	Remote Similarity	NPD6928	Phase 2
0.6	Remote Similarity	NPD5173	Approved
0.6	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD5223	Approved
0.5981	Remote Similarity	NPD6079	Approved
0.598	Remote Similarity	NPD4788	Approved
0.5968	Remote Similarity	NPD6370	Approved
0.5963	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5210	Approved
0.5963	Remote Similarity	NPD4629	Approved
0.5962	Remote Similarity	NPD6098	Approved
0.5952	Remote Similarity	NPD6336	Discontinued
0.5946	Remote Similarity	NPD4225	Approved
0.5943	Remote Similarity	NPD6904	Approved
0.5943	Remote Similarity	NPD6080	Approved
0.5943	Remote Similarity	NPD6673	Approved
0.5941	Remote Similarity	NPD1780	Approved
0.5941	Remote Similarity	NPD1779	Approved
0.5929	Remote Similarity	NPD5211	Phase 2
0.5929	Remote Similarity	NPD5226	Approved
0.5929	Remote Similarity	NPD5224	Approved
0.5929	Remote Similarity	NPD7632	Discontinued
0.5929	Remote Similarity	NPD5225	Approved
0.5929	Remote Similarity	NPD4633	Approved
0.5926	Remote Similarity	NPD8171	Discontinued
0.5922	Remote Similarity	NPD4786	Approved
0.5913	Remote Similarity	NPD6008	Approved
0.5909	Remote Similarity	NPD7614	Phase 1
0.5905	Remote Similarity	NPD3573	Approved
0.59	Remote Similarity	NPD7645	Phase 2
0.5895	Remote Similarity	NPD4787	Phase 1
0.5887	Remote Similarity	NPD6016	Approved
0.5887	Remote Similarity	NPD6015	Approved
0.5882	Remote Similarity	NPD3667	Approved
0.5877	Remote Similarity	NPD5175	Approved
0.5877	Remote Similarity	NPD4754	Approved
0.5877	Remote Similarity	NPD5174	Approved
0.5868	Remote Similarity	NPD6940	Discontinued
0.5847	Remote Similarity	NPD4634	Approved
0.584	Remote Similarity	NPD5988	Approved
0.5827	Remote Similarity	NPD7507	Approved
0.5826	Remote Similarity	NPD5141	Approved
0.5825	Remote Similarity	NPD3669	Approved
0.5825	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.581	Remote Similarity	NPD7334	Approved
0.581	Remote Similarity	NPD6684	Approved
0.581	Remote Similarity	NPD5330	Approved
0.581	Remote Similarity	NPD7146	Approved
0.581	Remote Similarity	NPD6409	Approved
0.581	Remote Similarity	NPD7521	Approved
0.5794	Remote Similarity	NPD4753	Phase 2
0.578	Remote Similarity	NPD4202	Approved
0.5776	Remote Similarity	NPD4767	Approved
0.5776	Remote Similarity	NPD4768	Approved
0.5766	Remote Similarity	NPD7732	Phase 3
0.5736	Remote Similarity	NPD6033	Approved
0.5726	Remote Similarity	NPD6412	Phase 2
0.5726	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD6903	Approved
0.5692	Remote Similarity	NPD7319	Approved
0.569	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.569	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD6411	Approved
0.5688	Remote Similarity	NPD5693	Phase 1
0.5688	Remote Similarity	NPD6050	Approved
0.5686	Remote Similarity	NPD7525	Registered
0.5684	Remote Similarity	NPD229	Approved
0.5678	Remote Similarity	NPD4730	Approved
0.5678	Remote Similarity	NPD4729	Approved
0.5678	Remote Similarity	NPD5128	Approved
0.5667	Remote Similarity	NPD3198	Approved
0.566	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD4802	Phase 2
0.5644	Remote Similarity	NPD3617	Approved
0.5644	Remote Similarity	NPD4238	Approved
0.5632	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD3665	Phase 1
0.5619	Remote Similarity	NPD3666	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