NPASS Compound

Structure

CID69713 OpenBabel06191715402D 39 41 0 0 1 0 0 0 0 0999 V2000 -0.6766 -3.8370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2533 -3.8772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4076 0.9191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4923 -1.6403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6000 -0.8202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3232 2.2114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9740 -3.3742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9592 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2522 1.4923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2892 -0.4130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5919 -4.1701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0693 0.3331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4923 0.6663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8306 -0.6663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4870 0.8435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3380 -3.5440 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6615 0.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4923 -0.6663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7564 -0.3331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4079 2.5446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4870 -2.5306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0693 -0.3331 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0844 -1.2924 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1691 0.9592 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7462 0.6261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9153 -0.3331 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1691 -0.9592 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4870 -0.8435 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1689 -2.5848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9153 0.3331 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7564 0.6409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2387 3.5038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4870 -2.5306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9150 -1.9587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9129 -0.8202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3383 1.9185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9740 -1.6871 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2536 -2.2516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 3 17 1 0 0 0 0 4 18 2 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 8 30 1 0 0 0 0 9 30 1 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 31 1 0 0 0 0 14 17 1 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 15 31 1 0 0 0 0 16 2 1 6 0 0 0 16 29 1 0 0 0 0 17 25 2 0 0 0 0 18 22 1 0 0 0 0 18 26 1 0 0 0 0 19 32 2 0 0 0 0 19 36 1 0 0 0 0 20 33 2 0 0 0 0 20 37 1 0 0 0 0 21 34 2 0 0 0 0 21 38 1 0 0 0 0 22 36 1 6 0 0 0 23 27 1 0 0 0 0 23 39 1 1 0 0 0 24 25 1 0 0 0 0 24 37 1 1 0 0 0 25 30 1 0 0 0 0 26 28 1 0 0 0 0 26 31 1 1 0 0 0 27 28 1 0 0 0 0 27 30 1 6 0 0 0 28 38 1 6 0 0 0 29 35 2 0 0 0 0 29 39 1 0 0 0 0 31 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.32
Volume:	573.566
LogP:	5.544
LogD:	3.486
LogS:	-4.529
# Rotatable Bonds:	10
TPSA:	105.2
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.245
Synthetic Accessibility Score:	5.821
Fsp3:	0.742
Lipinski Rule-of-5:	Rejected
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:	-4.851
MDCK Permeability:	7.107650162652135e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.53
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.163
Plasma Protein Binding (PPB):	74.81787109375%
Volume Distribution (VD):	2.206
Pgp-substrate:	22.735755920410156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.037
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.409
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.353
CYP2D6-substrate:	0.04
CYP3A4-inhibitor:	0.633
CYP3A4-substrate:	0.585

ADMET: Excretion

Clearance (CL):	6.632
Half-life (T1/2):	0.002

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.948
Drug-inuced Liver Injury (DILI):	0.924
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.933
Maximum Recommended Daily Dose:	0.707
Skin Sensitization:	0.222
Carcinogencity:	0.239
Eye Corrosion:	0.294
Eye Irritation:	0.027
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC69713

Natural Product ID:	NPC69713
*Common Name:**	USNOOZXSAIYFCE-XQOWVITFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	USNOOZXSAIYFCE-XQOWVITFSA-N
Standard InCHI:	InChI=1S/C31H46O8/c1-11-16(2)29(35)39-23-14-17(3)25-24(37-20(6)33)15-31(10)13-12-22(36-19(5)32)18(4)26(31)28(38-21(7)34)27(23)30(25,8)9/h16,22-24,26-28H,4,11-15H2,1-3,5-10H3/t16-,22-,23-,24-,26-,27-,28-,31-/m0/s1
SMILES:	CC[C@H](C)C(=O)O[C@H]1CC(=C2[C@H](C[C@]3(C)CC[C@@H](C(=C)[C@H]3[C@@H]([C@H]1C2(C)C)OC(=O)C)OC(=O)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465852
PubChem CID:	11049885
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes and derivatives

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12217376]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	n.a.	n.a.	PMID[12444707]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	Yunnang Province, China	2000-OCT	PMID[21138310]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	xylem	n.a.	PMID[21138310]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15125.1	Taxus wallichiana var. chinensis	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15125.1	Taxus wallichiana var. chinensis	Varieties	Taxaceae	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
EC50	2
IC50	1

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	229086765.28	nM	PMID[454572]
NPT453	Cell Line	HT-1080	Homo sapiens	EC50	=	84.9	ug.mL-1	PMID[454573]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	84.1	ug.mL-1	PMID[454573]

☑ 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 NPC69713 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	219
0.1-0.2	1470
0.2-0.3	4881
0.3-0.4	12003
0.4-0.5	11831
0.5-0.6	7656
0.6-0.7	4223
0.7-0.8	367
0.8-0.85	26
0.85-0.9	9
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC102640
0.9756	High Similarity	NPC102996
0.9318	High Similarity	NPC471786
0.9318	High Similarity	NPC37603
0.931	High Similarity	NPC99653
0.9195	High Similarity	NPC124374
0.9186	High Similarity	NPC261320
0.908	High Similarity	NPC48732
0.908	High Similarity	NPC220216
0.8953	High Similarity	NPC471779
0.8791	High Similarity	NPC284194
0.8791	High Similarity	NPC211810
0.8791	High Similarity	NPC471765
0.8791	High Similarity	NPC221801
0.8778	High Similarity	NPC472360
0.8778	High Similarity	NPC472416
0.8602	High Similarity	NPC471366
0.8602	High Similarity	NPC476800
0.8602	High Similarity	NPC472186
0.8602	High Similarity	NPC318917
0.8571	High Similarity	NPC105375
0.8571	High Similarity	NPC469802
0.8571	High Similarity	NPC182826
0.8511	High Similarity	NPC473204
0.8511	High Similarity	NPC473545
0.8511	High Similarity	NPC472187
0.8495	Intermediate Similarity	NPC472188
0.8454	Intermediate Similarity	NPC111952
0.8438	Intermediate Similarity	NPC8196
0.8387	Intermediate Similarity	NPC171598
0.8387	Intermediate Similarity	NPC129569
0.8367	Intermediate Similarity	NPC143609
0.8352	Intermediate Similarity	NPC477574
0.8333	Intermediate Similarity	NPC137430
0.8333	Intermediate Similarity	NPC246028
0.8298	Intermediate Similarity	NPC473244
0.8298	Intermediate Similarity	NPC100912
0.828	Intermediate Similarity	NPC472189
0.828	Intermediate Similarity	NPC471372
0.828	Intermediate Similarity	NPC471362
0.8265	Intermediate Similarity	NPC472389
0.8256	Intermediate Similarity	NPC25554
0.8247	Intermediate Similarity	NPC99266
0.8247	Intermediate Similarity	NPC7644
0.8247	Intermediate Similarity	NPC127933
0.8247	Intermediate Similarity	NPC7613
0.8247	Intermediate Similarity	NPC475889
0.8211	Intermediate Similarity	NPC107806
0.8211	Intermediate Similarity	NPC72647
0.8191	Intermediate Similarity	NPC475380
0.8191	Intermediate Similarity	NPC209297
0.8172	Intermediate Similarity	NPC140277
0.8172	Intermediate Similarity	NPC88507
0.8163	Intermediate Similarity	NPC201880
0.8163	Intermediate Similarity	NPC81567
0.8163	Intermediate Similarity	NPC473207
0.8163	Intermediate Similarity	NPC470321
0.8163	Intermediate Similarity	NPC264867
0.8161	Intermediate Similarity	NPC471218
0.8152	Intermediate Similarity	NPC473944
0.8144	Intermediate Similarity	NPC238397
0.8144	Intermediate Similarity	NPC471363
0.8144	Intermediate Similarity	NPC472552
0.8125	Intermediate Similarity	NPC271295
0.8125	Intermediate Similarity	NPC79303
0.8125	Intermediate Similarity	NPC188968
0.8105	Intermediate Similarity	NPC311241
0.8105	Intermediate Similarity	NPC475446
0.81	Intermediate Similarity	NPC151393
0.8061	Intermediate Similarity	NPC134270
0.8041	Intermediate Similarity	NPC97435
0.8041	Intermediate Similarity	NPC472554
0.8022	Intermediate Similarity	NPC477128
0.802	Intermediate Similarity	NPC475586
0.8	Intermediate Similarity	NPC125423
0.8	Intermediate Similarity	NPC472390
0.8	Intermediate Similarity	NPC88013
0.8	Intermediate Similarity	NPC94905
0.8	Intermediate Similarity	NPC194132
0.8	Intermediate Similarity	NPC184512
0.8	Intermediate Similarity	NPC8954
0.8	Intermediate Similarity	NPC311166
0.7978	Intermediate Similarity	NPC102048
0.7959	Intermediate Similarity	NPC475344
0.7959	Intermediate Similarity	NPC476471
0.7957	Intermediate Similarity	NPC234335
0.7938	Intermediate Similarity	NPC476933
0.7921	Intermediate Similarity	NPC128795
0.7921	Intermediate Similarity	NPC217921
0.7921	Intermediate Similarity	NPC48548
0.7921	Intermediate Similarity	NPC135015
0.7921	Intermediate Similarity	NPC311223
0.7921	Intermediate Similarity	NPC472439
0.7921	Intermediate Similarity	NPC469916
0.7912	Intermediate Similarity	NPC476600
0.79	Intermediate Similarity	NPC252296
0.7895	Intermediate Similarity	NPC276110
0.7889	Intermediate Similarity	NPC35933
0.7879	Intermediate Similarity	NPC254202
0.7879	Intermediate Similarity	NPC474124
0.7872	Intermediate Similarity	NPC475657
0.7872	Intermediate Similarity	NPC7349
0.7865	Intermediate Similarity	NPC12283
0.7865	Intermediate Similarity	NPC474193
0.7857	Intermediate Similarity	NPC475617
0.7857	Intermediate Similarity	NPC476478
0.7849	Intermediate Similarity	NPC475776
0.7843	Intermediate Similarity	NPC316974
0.7843	Intermediate Similarity	NPC40728
0.7835	Intermediate Similarity	NPC216478
0.7826	Intermediate Similarity	NPC106332
0.7826	Intermediate Similarity	NPC470612
0.7826	Intermediate Similarity	NPC93411
0.7826	Intermediate Similarity	NPC470613
0.7822	Intermediate Similarity	NPC112780
0.7822	Intermediate Similarity	NPC473586
0.7816	Intermediate Similarity	NPC242767
0.7812	Intermediate Similarity	NPC165632
0.7802	Intermediate Similarity	NPC286153
0.7802	Intermediate Similarity	NPC471219
0.7802	Intermediate Similarity	NPC220478
0.78	Intermediate Similarity	NPC473577
0.78	Intermediate Similarity	NPC474550
0.78	Intermediate Similarity	NPC475585
0.78	Intermediate Similarity	NPC473543
0.7789	Intermediate Similarity	NPC161998
0.7789	Intermediate Similarity	NPC470697
0.7789	Intermediate Similarity	NPC250075
0.7789	Intermediate Similarity	NPC105490
0.7778	Intermediate Similarity	NPC31058
0.7778	Intermediate Similarity	NPC469606
0.7778	Intermediate Similarity	NPC165250
0.7778	Intermediate Similarity	NPC273005
0.7778	Intermediate Similarity	NPC475038
0.7778	Intermediate Similarity	NPC476081
0.7778	Intermediate Similarity	NPC109195
0.7767	Intermediate Similarity	NPC472417
0.7767	Intermediate Similarity	NPC119550
0.7767	Intermediate Similarity	NPC469917
0.7755	Intermediate Similarity	NPC477968
0.7755	Intermediate Similarity	NPC477972
0.7755	Intermediate Similarity	NPC219285
0.7755	Intermediate Similarity	NPC161527
0.7755	Intermediate Similarity	NPC477971
0.7755	Intermediate Similarity	NPC228251
0.7755	Intermediate Similarity	NPC20113
0.7753	Intermediate Similarity	NPC256112
0.7745	Intermediate Similarity	NPC475263
0.7745	Intermediate Similarity	NPC476479
0.7742	Intermediate Similarity	NPC314727
0.7742	Intermediate Similarity	NPC284561
0.7732	Intermediate Similarity	NPC285513
0.7727	Intermediate Similarity	NPC233332
0.7723	Intermediate Similarity	NPC475290
0.7717	Intermediate Similarity	NPC175293
0.7717	Intermediate Similarity	NPC166857
0.7708	Intermediate Similarity	NPC281134
0.7708	Intermediate Similarity	NPC476519
0.77	Intermediate Similarity	NPC473523
0.77	Intermediate Similarity	NPC23584
0.7692	Intermediate Similarity	NPC474013
0.7684	Intermediate Similarity	NPC473678
0.7677	Intermediate Similarity	NPC476132
0.7677	Intermediate Similarity	NPC11974
0.7667	Intermediate Similarity	NPC127917
0.7667	Intermediate Similarity	NPC222358
0.766	Intermediate Similarity	NPC232202
0.766	Intermediate Similarity	NPC78973
0.7653	Intermediate Similarity	NPC264378
0.7647	Intermediate Similarity	NPC109376
0.7647	Intermediate Similarity	NPC216636
0.7647	Intermediate Similarity	NPC475781
0.7634	Intermediate Similarity	NPC473879
0.7629	Intermediate Similarity	NPC202833
0.7624	Intermediate Similarity	NPC470297
0.7609	Intermediate Similarity	NPC473226
0.7609	Intermediate Similarity	NPC329692
0.7604	Intermediate Similarity	NPC473434
0.7604	Intermediate Similarity	NPC474922
0.7604	Intermediate Similarity	NPC477129
0.7604	Intermediate Similarity	NPC477130
0.7604	Intermediate Similarity	NPC471446
0.7604	Intermediate Similarity	NPC38830
0.7604	Intermediate Similarity	NPC474841
0.7604	Intermediate Similarity	NPC57117
0.76	Intermediate Similarity	NPC11956
0.76	Intermediate Similarity	NPC183571
0.76	Intermediate Similarity	NPC295791
0.76	Intermediate Similarity	NPC162973
0.76	Intermediate Similarity	NPC474709
0.7586	Intermediate Similarity	NPC189206
0.7582	Intermediate Similarity	NPC159635
0.7582	Intermediate Similarity	NPC96055
0.7579	Intermediate Similarity	NPC474631
0.7579	Intermediate Similarity	NPC476417
0.7579	Intermediate Similarity	NPC72845
0.7579	Intermediate Similarity	NPC41239
0.7579	Intermediate Similarity	NPC49420
0.7576	Intermediate Similarity	NPC272223
0.7576	Intermediate Similarity	NPC471413

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 NPC69713 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	1877
0.2-0.3	3917
0.3-0.4	2138
0.4-0.5	662
0.5-0.6	308
0.6-0.7	47
0.7-0.8	0
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
0.7653	Intermediate Similarity	NPD7638	Approved
0.7576	Intermediate Similarity	NPD7639	Approved
0.7576	Intermediate Similarity	NPD7640	Approved
0.7308	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6051	Approved
0.7174	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6399	Phase 3
0.7129	Intermediate Similarity	NPD4225	Approved
0.7103	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7632	Discontinued
0.7075	Intermediate Similarity	NPD6686	Approved
0.7071	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7900	Approved
0.7009	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5778	Approved
0.697	Remote Similarity	NPD5779	Approved
0.6947	Remote Similarity	NPD1694	Approved
0.6939	Remote Similarity	NPD46	Approved
0.6939	Remote Similarity	NPD6698	Approved
0.69	Remote Similarity	NPD7748	Approved
0.6893	Remote Similarity	NPD6648	Approved
0.6887	Remote Similarity	NPD6008	Approved
0.6875	Remote Similarity	NPD7146	Approved
0.6875	Remote Similarity	NPD5330	Approved
0.6875	Remote Similarity	NPD6684	Approved
0.6875	Remote Similarity	NPD7521	Approved
0.6875	Remote Similarity	NPD6409	Approved
0.6875	Remote Similarity	NPD7334	Approved
0.6869	Remote Similarity	NPD7637	Suspended
0.6863	Remote Similarity	NPD7902	Approved
0.6827	Remote Similarity	NPD5344	Discontinued
0.6778	Remote Similarity	NPD8039	Approved
0.6768	Remote Similarity	NPD7838	Discovery
0.6735	Remote Similarity	NPD5737	Approved
0.6735	Remote Similarity	NPD6672	Approved
0.6735	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6903	Approved
0.67	Remote Similarity	NPD6411	Approved
0.67	Remote Similarity	NPD7515	Phase 2
0.6697	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD6053	Discontinued
0.6638	Remote Similarity	NPD8033	Approved
0.6609	Remote Similarity	NPD7516	Approved
0.6607	Remote Similarity	NPD8133	Approved
0.6579	Remote Similarity	NPD7115	Discovery
0.6574	Remote Similarity	NPD5739	Approved
0.6574	Remote Similarity	NPD7128	Approved
0.6574	Remote Similarity	NPD6675	Approved
0.6574	Remote Similarity	NPD6402	Approved
0.6555	Remote Similarity	NPD7507	Approved
0.6552	Remote Similarity	NPD8294	Approved
0.6552	Remote Similarity	NPD8377	Approved
0.6545	Remote Similarity	NPD6373	Approved
0.6545	Remote Similarity	NPD6372	Approved
0.6535	Remote Similarity	NPD8034	Phase 2
0.6535	Remote Similarity	NPD5693	Phase 1
0.6535	Remote Similarity	NPD8035	Phase 2
0.65	Remote Similarity	NPD6101	Approved
0.65	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD8335	Approved
0.6496	Remote Similarity	NPD8380	Approved
0.6496	Remote Similarity	NPD8379	Approved
0.6496	Remote Similarity	NPD7503	Approved
0.6496	Remote Similarity	NPD8378	Approved
0.6496	Remote Similarity	NPD8296	Approved
0.6495	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD3668	Phase 3
0.6495	Remote Similarity	NPD4786	Approved
0.6489	Remote Similarity	NPD7645	Phase 2
0.6476	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD3573	Approved
0.6458	Remote Similarity	NPD3667	Approved
0.6455	Remote Similarity	NPD6881	Approved
0.6455	Remote Similarity	NPD7320	Approved
0.6455	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6899	Approved
0.6435	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6650	Approved
0.6429	Remote Similarity	NPD6649	Approved
0.6395	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7319	Approved
0.6392	Remote Similarity	NPD6695	Phase 3
0.6381	Remote Similarity	NPD6083	Phase 2
0.6381	Remote Similarity	NPD6084	Phase 2
0.6373	Remote Similarity	NPD7983	Approved
0.6372	Remote Similarity	NPD8297	Approved
0.6372	Remote Similarity	NPD6882	Approved
0.6364	Remote Similarity	NPD6412	Phase 2
0.6364	Remote Similarity	NPD5697	Approved
0.6364	Remote Similarity	NPD6098	Approved
0.6364	Remote Similarity	NPD5701	Approved
0.6346	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5695	Phase 3
0.6339	Remote Similarity	NPD7290	Approved
0.6339	Remote Similarity	NPD6883	Approved
0.6339	Remote Similarity	NPD7102	Approved
0.6337	Remote Similarity	NPD6904	Approved
0.6337	Remote Similarity	NPD6080	Approved
0.6337	Remote Similarity	NPD6673	Approved
0.6337	Remote Similarity	NPD1695	Approved
0.63	Remote Similarity	NPD4251	Approved
0.63	Remote Similarity	NPD4250	Approved
0.6283	Remote Similarity	NPD6847	Approved
0.6283	Remote Similarity	NPD6869	Approved
0.6283	Remote Similarity	NPD6617	Approved
0.6283	Remote Similarity	NPD8130	Phase 1
0.6271	Remote Similarity	NPD6319	Approved
0.6263	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8328	Phase 3
0.625	Remote Similarity	NPD7525	Registered
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6013	Approved
0.6237	Remote Similarity	NPD6942	Approved
0.6237	Remote Similarity	NPD7339	Approved
0.6237	Remote Similarity	NPD8264	Approved
0.6218	Remote Similarity	NPD8513	Phase 3
0.6218	Remote Similarity	NPD8516	Approved
0.6218	Remote Similarity	NPD8517	Approved
0.6218	Remote Similarity	NPD8515	Approved
0.6216	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6050	Approved
0.62	Remote Similarity	NPD3618	Phase 1
0.62	Remote Similarity	NPD4249	Approved
0.6195	Remote Similarity	NPD6371	Approved
0.6176	Remote Similarity	NPD5328	Approved
0.6174	Remote Similarity	NPD4632	Approved
0.617	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5696	Approved
0.6161	Remote Similarity	NPD6011	Approved
0.6146	Remote Similarity	NPD6929	Approved
0.614	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7750	Discontinued
0.6139	Remote Similarity	NPD7524	Approved
0.6139	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5209	Approved
0.6117	Remote Similarity	NPD5692	Phase 3
0.61	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD6931	Approved
0.6082	Remote Similarity	NPD4820	Approved
0.6082	Remote Similarity	NPD4822	Approved
0.6082	Remote Similarity	NPD4821	Approved
0.6082	Remote Similarity	NPD6930	Phase 2
0.6082	Remote Similarity	NPD4819	Approved
0.6078	Remote Similarity	NPD5208	Approved
0.6075	Remote Similarity	NPD4755	Approved
0.6066	Remote Similarity	NPD7492	Approved
0.6061	Remote Similarity	NPD7154	Phase 3
0.6058	Remote Similarity	NPD6079	Approved
0.6058	Remote Similarity	NPD5694	Approved
0.6042	Remote Similarity	NPD4268	Approved
0.6042	Remote Similarity	NPD4271	Approved
0.6038	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD7260	Phase 2
0.6019	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6009	Approved
0.6016	Remote Similarity	NPD6616	Approved
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD4202	Approved
0.6	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD6054	Approved
0.5984	Remote Similarity	NPD7604	Phase 2
0.5981	Remote Similarity	NPD7839	Suspended
0.5968	Remote Similarity	NPD8293	Discontinued
0.5968	Remote Similarity	NPD8074	Phase 3
0.5968	Remote Similarity	NPD7078	Approved
0.5963	Remote Similarity	NPD4700	Approved
0.5963	Remote Similarity	NPD5286	Approved
0.5963	Remote Similarity	NPD4696	Approved
0.5963	Remote Similarity	NPD5285	Approved
0.5962	Remote Similarity	NPD5785	Approved
0.5962	Remote Similarity	NPD5207	Approved
0.5962	Remote Similarity	NPD3168	Discontinued
0.595	Remote Similarity	NPD6921	Approved
0.595	Remote Similarity	NPD5983	Phase 2
0.5943	Remote Similarity	NPD6001	Approved
0.5943	Remote Similarity	NPD5282	Discontinued
0.5938	Remote Similarity	NPD5776	Phase 2
0.5938	Remote Similarity	NPD6925	Approved
0.5932	Remote Similarity	NPD6274	Approved
0.592	Remote Similarity	NPD7736	Approved
0.5918	Remote Similarity	NPD7332	Phase 2
0.5918	Remote Similarity	NPD4695	Discontinued
0.5918	Remote Similarity	NPD7514	Phase 3
0.5917	Remote Similarity	NPD7100	Approved
0.5917	Remote Similarity	NPD7101	Approved
0.5905	Remote Similarity	NPD5284	Approved
0.5905	Remote Similarity	NPD5281	Approved
0.5905	Remote Similarity	NPD7087	Discontinued
0.5902	Remote Similarity	NPD6370	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