NPASS Compound

Structure

CID11895 OpenBabel06191715342D 34 39 0 0 1 0 0 0 0 0999 V2000 5.7889 4.2927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7018 3.8861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3868 0.0497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2658 0.4735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7233 -0.9950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8471 -1.4672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 -1.9566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2373 2.4463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3902 2.9354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8474 -0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4368 2.6362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5425 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0911 3.3628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0475 3.1595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0846 0.9796 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2379 1.4685 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5430 1.4682 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6953 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7389 1.7062 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8479 -1.4677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3901 0.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6954 0.9788 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8477 1.4682 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9788 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3496 2.2296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3902 0.9791 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8476 -0.4894 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7139 -1.9677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2562 -0.4997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3060 2.0262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6953 1.5029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 7 2 0 0 0 0 6 10 1 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 28 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 14 2 0 0 0 0 14 25 1 0 0 0 0 15 3 1 1 0 0 0 15 16 1 0 0 0 0 16 26 1 6 0 0 0 17 22 1 0 0 0 0 17 26 1 6 0 0 0 18 22 1 0 0 0 0 18 27 1 6 0 0 0 19 15 1 1 0 0 0 19 33 1 0 0 0 0 20 27 1 0 0 0 0 20 29 2 0 0 0 0 21 26 1 1 0 0 0 21 30 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 23 34 1 0 0 0 0 24 28 1 0 0 0 0 24 34 1 0 0 0 0 25 31 2 0 0 0 0 25 33 1 0 0 0 0 27 28 1 0 0 0 0 28 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.27
Volume:	483.701
LogP:	3.74
LogD:	3.945
LogS:	-4.194
# Rotatable Bonds:	2
TPSA:	96.36
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.365
Synthetic Accessibility Score:	5.623
Fsp3:	0.786
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:	-4.776
MDCK Permeability:	2.08451492653694e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.964
Human Intestinal Absorption (HIA):	0.058
20% Bioavailability (F20%):	0.077
30% Bioavailability (F30%):	0.278

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.949
Plasma Protein Binding (PPB):	68.87101745605469%
Volume Distribution (VD):	1.378
Pgp-substrate:	22.854732513427734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.353
CYP2C19-inhibitor:	0.187
CYP2C19-substrate:	0.754
CYP2C9-inhibitor:	0.244
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.152
CYP3A4-inhibitor:	0.851
CYP3A4-substrate:	0.585

ADMET: Excretion

Clearance (CL):	10.447
Half-life (T1/2):	0.891

ADMET: Toxicity

hERG Blockers:	0.376
Human Hepatotoxicity (H-HT):	0.288
Drug-inuced Liver Injury (DILI):	0.088
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.947
Maximum Recommended Daily Dose:	0.858
Skin Sensitization:	0.346
Carcinogencity:	0.436
Eye Corrosion:	0.027
Eye Irritation:	0.068
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: NPC11895

Natural Product ID:	NPC11895
*Common Name:**	Withaferoxolide
IUPAC Name:	n.a.
Synonyms:	Withaferoxolide
Standard InCHIKey:	DGZBYFRXLDYRMK-XLVSLIJYSA-N
Standard InCHI:	InChI=1S/C28H38O6/c1-13-11-19(33-25(31)14(13)2)15(3)16-8-9-17-22-18(12-21(30)26(16,17)4)27(5)20(29)7-6-10-28(27,32)24-23(22)34-24/h6-7,15-19,21-24,30,32H,8-12H2,1-5H3/t15-,16+,17-,18-,19+,21-,22-,23-,24-,26+,27-,28-/m0/s1
SMILES:	CC1=C(C)C(=O)O[C@H](C1)[C@H]([C@H]1CC[C@@H]2[C@]1(C)[C@@H](O)C[C@H]1[C@H]2[C@@H]2O[C@@H]2[C@@]2([C@]1(C)C(=O)C=CC2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446585
PubChem CID:	44566979
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO13689	Datura ferox	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO10976	Nicandra physalodes	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13689	Datura ferox	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10976	Nicandra physalodes	Species	Solanaceae	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
Others	3

Activity Type	# Activity
Individual Protein	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CQ	=	40.8	uM	PMID[471442]
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	14.5	uM	PMID[471442]
NPT2	Others	Unspecified		Ratio	>	2.9	n.a.	PMID[471442]
NPT27	Others	Unspecified		IC50	>	42500.0	nM	PMID[471442]

☑ 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 NPC11895 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	254
0.1-0.2	1406
0.2-0.3	4017
0.3-0.4	6913
0.4-0.5	12042
0.5-0.6	8187
0.6-0.7	6490
0.7-0.8	2888
0.8-0.85	339
0.85-0.9	106
0.9-0.95	45
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9912	High Similarity	NPC170538
0.9826	High Similarity	NPC293112
0.9739	High Similarity	NPC172154
0.9739	High Similarity	NPC81736
0.9655	High Similarity	NPC473635
0.9652	High Similarity	NPC469789
0.9569	High Similarity	NPC8369
0.9478	High Similarity	NPC67569
0.9397	High Similarity	NPC23786
0.9397	High Similarity	NPC470265
0.9298	High Similarity	NPC286528
0.9298	High Similarity	NPC20302
0.9298	High Similarity	NPC167606
0.9298	High Similarity	NPC140055
0.9224	High Similarity	NPC268530
0.9224	High Similarity	NPC154491
0.9224	High Similarity	NPC476961
0.9224	High Similarity	NPC251226
0.9217	High Similarity	NPC709
0.9217	High Similarity	NPC50774
0.9145	High Similarity	NPC159456
0.9145	High Similarity	NPC4021
0.9138	High Similarity	NPC476960
0.9138	High Similarity	NPC264954
0.9138	High Similarity	NPC42673
0.9138	High Similarity	NPC475520
0.913	High Similarity	NPC312824
0.913	High Similarity	NPC470492
0.913	High Similarity	NPC183580
0.913	High Similarity	NPC470493
0.9123	High Similarity	NPC147912
0.9123	High Similarity	NPC67259
0.9091	High Similarity	NPC231529
0.9076	High Similarity	NPC8374
0.9068	High Similarity	NPC269642
0.906	High Similarity	NPC474370
0.9043	High Similarity	NPC270929
0.9035	High Similarity	NPC122056
0.8992	High Similarity	NPC204812
0.8992	High Similarity	NPC120724
0.8983	High Similarity	NPC46570
0.8974	High Similarity	NPC475041
0.8974	High Similarity	NPC230513
0.8966	High Similarity	NPC469684
0.8966	High Similarity	NPC470959
0.8966	High Similarity	NPC476965
0.8957	High Similarity	NPC284915
0.8934	High Similarity	NPC473593
0.8926	High Similarity	NPC287423
0.8917	High Similarity	NPC241456
0.8917	High Similarity	NPC469790
0.8917	High Similarity	NPC32868
0.8908	High Similarity	NPC153700
0.8908	High Similarity	NPC88326
0.8908	High Similarity	NPC107493
0.8889	High Similarity	NPC473720
0.8889	High Similarity	NPC329736
0.8889	High Similarity	NPC284707
0.886	High Similarity	NPC474229
0.8852	High Similarity	NPC473620
0.8843	High Similarity	NPC120994
0.8843	High Similarity	NPC203702
0.8833	High Similarity	NPC473979
0.8814	High Similarity	NPC61520
0.8814	High Similarity	NPC473274
0.8803	High Similarity	NPC53396
0.8803	High Similarity	NPC98249
0.8803	High Similarity	NPC58662
0.8803	High Similarity	NPC55296
0.8793	High Similarity	NPC238667
0.879	High Similarity	NPC231240
0.878	High Similarity	NPC476966
0.877	High Similarity	NPC473253
0.876	High Similarity	NPC3381
0.876	High Similarity	NPC470494
0.8739	High Similarity	NPC476962
0.8739	High Similarity	NPC79579
0.8729	High Similarity	NPC186525
0.8729	High Similarity	NPC153440
0.872	High Similarity	NPC316915
0.8718	High Similarity	NPC190286
0.8696	High Similarity	NPC469655
0.8696	High Similarity	NPC469656
0.8696	High Similarity	NPC474846
0.8667	High Similarity	NPC473256
0.8667	High Similarity	NPC470878
0.8667	High Similarity	NPC310511
0.8655	High Similarity	NPC5292
0.8655	High Similarity	NPC77689
0.8655	High Similarity	NPC473203
0.8655	High Similarity	NPC473636
0.8644	High Similarity	NPC474518
0.8644	High Similarity	NPC134430
0.8644	High Similarity	NPC243065
0.8644	High Similarity	NPC284068
0.8632	High Similarity	NPC474181
0.8632	High Similarity	NPC470953
0.8629	High Similarity	NPC470880
0.8621	High Similarity	NPC269530
0.8621	High Similarity	NPC236217
0.8618	High Similarity	NPC470882
0.8618	High Similarity	NPC42399
0.8609	High Similarity	NPC472215
0.8609	High Similarity	NPC472214
0.8609	High Similarity	NPC37116
0.8609	High Similarity	NPC253906
0.8607	High Similarity	NPC24651
0.8583	High Similarity	NPC474585
0.8571	High Similarity	NPC311554
0.8571	High Similarity	NPC257457
0.8559	High Similarity	NPC176840
0.8559	High Similarity	NPC64318
0.8548	High Similarity	NPC245094
0.8547	High Similarity	NPC317210
0.8547	High Similarity	NPC25909
0.8534	High Similarity	NPC474315
0.8534	High Similarity	NPC470960
0.8525	High Similarity	NPC91693
0.8525	High Similarity	NPC18945
0.8525	High Similarity	NPC265557
0.8525	High Similarity	NPC105926
0.8525	High Similarity	NPC67251
0.8522	High Similarity	NPC284828
0.8522	High Similarity	NPC5475
0.8522	High Similarity	NPC173905
0.8522	High Similarity	NPC472216
0.8522	High Similarity	NPC469370
0.85	High Similarity	NPC305260
0.85	High Similarity	NPC473839
0.85	High Similarity	NPC472667
0.85	High Similarity	NPC211093
0.85	High Similarity	NPC473270
0.85	High Similarity	NPC270850
0.8492	Intermediate Similarity	NPC471855
0.8487	Intermediate Similarity	NPC476959
0.8487	Intermediate Similarity	NPC475809
0.8487	Intermediate Similarity	NPC13713
0.8487	Intermediate Similarity	NPC239273
0.8487	Intermediate Similarity	NPC478204
0.8475	Intermediate Similarity	NPC243354
0.8468	Intermediate Similarity	NPC473265
0.8462	Intermediate Similarity	NPC191620
0.8462	Intermediate Similarity	NPC476163
0.8462	Intermediate Similarity	NPC277769
0.8462	Intermediate Similarity	NPC476801
0.8455	Intermediate Similarity	NPC476729
0.8455	Intermediate Similarity	NPC473255
0.8455	Intermediate Similarity	NPC470922
0.8448	Intermediate Similarity	NPC29133
0.8448	Intermediate Similarity	NPC76084
0.8448	Intermediate Similarity	NPC473627
0.8443	Intermediate Similarity	NPC312833
0.8417	Intermediate Similarity	NPC478205
0.8417	Intermediate Similarity	NPC146280
0.8417	Intermediate Similarity	NPC108581
0.8417	Intermediate Similarity	NPC251310
0.8417	Intermediate Similarity	NPC124676
0.8417	Intermediate Similarity	NPC478206
0.8417	Intermediate Similarity	NPC113448
0.8413	Intermediate Similarity	NPC173347
0.8403	Intermediate Similarity	NPC476963
0.8403	Intermediate Similarity	NPC470075
0.84	Intermediate Similarity	NPC311534
0.839	Intermediate Similarity	NPC250109
0.839	Intermediate Similarity	NPC477126
0.839	Intermediate Similarity	NPC194273
0.839	Intermediate Similarity	NPC962
0.8376	Intermediate Similarity	NPC471243
0.8376	Intermediate Similarity	NPC470961
0.8376	Intermediate Similarity	NPC470076
0.8374	Intermediate Similarity	NPC55602
0.8374	Intermediate Similarity	NPC473802
0.8362	Intermediate Similarity	NPC475065
0.8361	Intermediate Similarity	NPC102822
0.8361	Intermediate Similarity	NPC470779
0.8361	Intermediate Similarity	NPC477046
0.8348	Intermediate Similarity	NPC329048
0.8348	Intermediate Similarity	NPC330011
0.8348	Intermediate Similarity	NPC180744
0.8348	Intermediate Similarity	NPC91034
0.8348	Intermediate Similarity	NPC263729
0.8347	Intermediate Similarity	NPC475775
0.8347	Intermediate Similarity	NPC476529
0.8333	Intermediate Similarity	NPC470854
0.8333	Intermediate Similarity	NPC221414
0.8333	Intermediate Similarity	NPC474654
0.8333	Intermediate Similarity	NPC287343
0.8333	Intermediate Similarity	NPC473656
0.8333	Intermediate Similarity	NPC122033
0.8333	Intermediate Similarity	NPC471854
0.8333	Intermediate Similarity	NPC473590
0.8333	Intermediate Similarity	NPC97908
0.8333	Intermediate Similarity	NPC35109
0.8333	Intermediate Similarity	NPC471407
0.8333	Intermediate Similarity	NPC473968
0.832	Intermediate Similarity	NPC298841
0.8319	Intermediate Similarity	NPC117712
0.8306	Intermediate Similarity	NPC473919
0.8306	Intermediate Similarity	NPC473709
0.8306	Intermediate Similarity	NPC318135

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 NPC11895 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	1568
0.2-0.3	3588
0.3-0.4	2416
0.4-0.5	782
0.5-0.6	303
0.6-0.7	171
0.7-0.8	99
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9298	High Similarity	NPD7115	Discovery
0.813	Intermediate Similarity	NPD6319	Approved
0.8051	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD7319	Approved
0.7966	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7934	Intermediate Similarity	NPD4632	Approved
0.7874	Intermediate Similarity	NPD7492	Approved
0.7851	Intermediate Similarity	NPD8297	Approved
0.784	Intermediate Similarity	NPD6054	Approved
0.7833	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7736	Approved
0.7815	Intermediate Similarity	NPD6881	Approved
0.7815	Intermediate Similarity	NPD6899	Approved
0.7812	Intermediate Similarity	NPD6616	Approved
0.7812	Intermediate Similarity	NPD7507	Approved
0.7797	Intermediate Similarity	NPD6008	Approved
0.7769	Intermediate Similarity	NPD6649	Approved
0.7769	Intermediate Similarity	NPD6650	Approved
0.7752	Intermediate Similarity	NPD7078	Approved
0.7739	Intermediate Similarity	NPD4225	Approved
0.7739	Intermediate Similarity	NPD7638	Approved
0.7731	Intermediate Similarity	NPD5697	Approved
0.7717	Intermediate Similarity	NPD6370	Approved
0.7686	Intermediate Similarity	NPD6883	Approved
0.7686	Intermediate Similarity	NPD7102	Approved
0.7686	Intermediate Similarity	NPD4634	Approved
0.7686	Intermediate Similarity	NPD7290	Approved
0.7672	Intermediate Similarity	NPD7640	Approved
0.7672	Intermediate Similarity	NPD7639	Approved
0.7656	Intermediate Similarity	NPD7604	Phase 2
0.7647	Intermediate Similarity	NPD6675	Approved
0.7647	Intermediate Similarity	NPD5739	Approved
0.7647	Intermediate Similarity	NPD6402	Approved
0.7647	Intermediate Similarity	NPD7128	Approved
0.7638	Intermediate Similarity	NPD6015	Approved
0.7638	Intermediate Similarity	NPD6016	Approved
0.7623	Intermediate Similarity	NPD6617	Approved
0.7623	Intermediate Similarity	NPD6869	Approved
0.7623	Intermediate Similarity	NPD6847	Approved
0.7623	Intermediate Similarity	NPD8130	Phase 1
0.7603	Intermediate Similarity	NPD6013	Approved
0.7603	Intermediate Similarity	NPD6012	Approved
0.7603	Intermediate Similarity	NPD6014	Approved
0.7603	Intermediate Similarity	NPD6372	Approved
0.7603	Intermediate Similarity	NPD6373	Approved
0.76	Intermediate Similarity	NPD6009	Approved
0.7583	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD5988	Approved
0.7561	Intermediate Similarity	NPD6882	Approved
0.7559	Intermediate Similarity	NPD6059	Approved
0.7522	Intermediate Similarity	NPD6079	Approved
0.7521	Intermediate Similarity	NPD6011	Approved
0.7521	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD7503	Approved
0.75	Intermediate Similarity	NPD5983	Phase 2
0.7481	Intermediate Similarity	NPD8293	Discontinued
0.748	Intermediate Similarity	NPD7516	Approved
0.7458	Intermediate Similarity	NPD5344	Discontinued
0.7438	Intermediate Similarity	NPD5701	Approved
0.7419	Intermediate Similarity	NPD6053	Discontinued
0.7405	Intermediate Similarity	NPD6336	Discontinued
0.7402	Intermediate Similarity	NPD7328	Approved
0.7402	Intermediate Similarity	NPD7327	Approved
0.7398	Intermediate Similarity	NPD6371	Approved
0.7395	Intermediate Similarity	NPD5211	Phase 2
0.7385	Intermediate Similarity	NPD8328	Phase 3
0.7377	Intermediate Similarity	NPD6686	Approved
0.7373	Intermediate Similarity	NPD5286	Approved
0.7373	Intermediate Similarity	NPD4696	Approved
0.7373	Intermediate Similarity	NPD5285	Approved
0.7364	Intermediate Similarity	NPD8513	Phase 3
0.7345	Intermediate Similarity	NPD5328	Approved
0.7304	Intermediate Similarity	NPD6399	Phase 3
0.7295	Intermediate Similarity	NPD6412	Phase 2
0.7273	Intermediate Similarity	NPD5141	Approved
0.7265	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD5222	Approved
0.7265	Intermediate Similarity	NPD5221	Approved
0.725	Intermediate Similarity	NPD5225	Approved
0.725	Intermediate Similarity	NPD4633	Approved
0.725	Intermediate Similarity	NPD5224	Approved
0.725	Intermediate Similarity	NPD5226	Approved
0.7231	Intermediate Similarity	NPD6921	Approved
0.7231	Intermediate Similarity	NPD8515	Approved
0.7231	Intermediate Similarity	NPD8378	Approved
0.7231	Intermediate Similarity	NPD8380	Approved
0.7231	Intermediate Similarity	NPD8335	Approved
0.7231	Intermediate Similarity	NPD8517	Approved
0.7231	Intermediate Similarity	NPD8033	Approved
0.7231	Intermediate Similarity	NPD8379	Approved
0.7231	Intermediate Similarity	NPD8516	Approved
0.7231	Intermediate Similarity	NPD8296	Approved
0.7209	Intermediate Similarity	NPD7101	Approved
0.7209	Intermediate Similarity	NPD7100	Approved
0.7203	Intermediate Similarity	NPD6084	Phase 2
0.7203	Intermediate Similarity	NPD5173	Approved
0.7203	Intermediate Similarity	NPD6083	Phase 2
0.7203	Intermediate Similarity	NPD4755	Approved
0.72	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5174	Approved
0.719	Intermediate Similarity	NPD5175	Approved
0.7167	Intermediate Similarity	NPD5223	Approved
0.7154	Intermediate Similarity	NPD8294	Approved
0.7154	Intermediate Similarity	NPD8377	Approved
0.7132	Intermediate Similarity	NPD6335	Approved
0.7119	Intermediate Similarity	NPD4697	Phase 3
0.7109	Intermediate Similarity	NPD6274	Approved
0.7109	Intermediate Similarity	NPD6868	Approved
0.7107	Intermediate Similarity	NPD7632	Discontinued
0.7094	Intermediate Similarity	NPD7748	Approved
0.7083	Intermediate Similarity	NPD4700	Approved
0.7083	Intermediate Similarity	NPD6648	Approved
0.708	Intermediate Similarity	NPD3618	Phase 1
0.7069	Intermediate Similarity	NPD7637	Suspended
0.7069	Intermediate Similarity	NPD7515	Phase 2
0.7059	Intermediate Similarity	NPD7902	Approved
0.7054	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6317	Approved
0.704	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6033	Approved
0.7034	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3573	Approved
0.7009	Intermediate Similarity	NPD5778	Approved
0.7009	Intermediate Similarity	NPD5779	Approved
0.7007	Intermediate Similarity	NPD7260	Phase 2
0.7	Intermediate Similarity	NPD6314	Approved
0.7	Intermediate Similarity	NPD6313	Approved
0.7	Intermediate Similarity	NPD5696	Approved
0.6983	Remote Similarity	NPD5785	Approved
0.6983	Remote Similarity	NPD46	Approved
0.6983	Remote Similarity	NPD6698	Approved
0.697	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.696	Remote Similarity	NPD4729	Approved
0.696	Remote Similarity	NPD4730	Approved
0.6953	Remote Similarity	NPD8133	Approved
0.693	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6411	Approved
0.6903	Remote Similarity	NPD4786	Approved
0.6891	Remote Similarity	NPD5210	Approved
0.6891	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5695	Phase 3
0.6891	Remote Similarity	NPD4629	Approved
0.688	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4202	Approved
0.685	Remote Similarity	NPD5250	Approved
0.685	Remote Similarity	NPD5251	Approved
0.685	Remote Similarity	NPD5248	Approved
0.685	Remote Similarity	NPD5249	Phase 3
0.685	Remote Similarity	NPD5247	Approved
0.6842	Remote Similarity	NPD6909	Approved
0.6842	Remote Similarity	NPD6908	Approved
0.6842	Remote Similarity	NPD1694	Approved
0.6838	Remote Similarity	NPD8074	Phase 3
0.6825	Remote Similarity	NPD5128	Approved
0.681	Remote Similarity	NPD5737	Approved
0.681	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6672	Approved
0.6807	Remote Similarity	NPD7900	Approved
0.6807	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4767	Approved
0.68	Remote Similarity	NPD4768	Approved
0.6797	Remote Similarity	NPD5215	Approved
0.6797	Remote Similarity	NPD5217	Approved
0.6797	Remote Similarity	NPD5216	Approved
0.6783	Remote Similarity	NPD6684	Approved
0.6783	Remote Similarity	NPD6409	Approved
0.6783	Remote Similarity	NPD7334	Approved
0.6783	Remote Similarity	NPD5330	Approved
0.6783	Remote Similarity	NPD7521	Approved
0.6783	Remote Similarity	NPD7146	Approved
0.678	Remote Similarity	NPD5693	Phase 1
0.678	Remote Similarity	NPD8035	Phase 2
0.678	Remote Similarity	NPD8034	Phase 2
0.6774	Remote Similarity	NPD4754	Approved
0.6752	Remote Similarity	NPD6101	Approved
0.6752	Remote Similarity	NPD4753	Phase 2
0.6752	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD3667	Approved
0.6724	Remote Similarity	NPD7524	Approved
0.6719	Remote Similarity	NPD5169	Approved
0.6719	Remote Similarity	NPD5135	Approved
0.6719	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7838	Discovery
0.6693	Remote Similarity	NPD5168	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6639	Remote Similarity	NPD5284	Approved
0.6639	Remote Similarity	NPD5281	Approved
0.6639	Remote Similarity	NPD7983	Approved
0.6613	Remote Similarity	NPD4159	Approved
0.661	Remote Similarity	NPD6080	Approved
0.661	Remote Similarity	NPD6904	Approved
0.661	Remote Similarity	NPD6673	Approved
0.6609	Remote Similarity	NPD3665	Phase 1
0.6609	Remote Similarity	NPD3133	Approved
0.6609	Remote Similarity	NPD3666	Approved
0.66	Remote Similarity	NPD7236	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