NPASS Compound

Structure

NPC470959 OpenBabel07101718222D 34 39 0 0 1 0 0 0 0 0999 V2000 -8.1470 0.0737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0519 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9932 -1.5698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4726 -0.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8545 -2.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2108 -0.2777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1854 -1.4612 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2072 -1.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4944 -0.5102 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6536 0.2550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.1417 -1.0454 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9626 1.2061 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 -6.8327 -1.9965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8898 0.1516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 4 27 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 22 1 0 0 0 0 7 8 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 28 1 0 0 0 0 11 25 1 0 0 0 0 12 23 1 0 0 0 0 13 26 1 0 0 0 0 14 33 1 0 0 0 0 15 24 1 0 0 0 0 15 26 1 0 0 0 0 16 12 1 1 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 14 1 6 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 18 25 1 6 0 0 0 19 25 1 6 0 0 0 20 27 1 6 0 0 0 21 13 1 6 0 0 0 21 34 1 0 0 0 0 22 27 1 0 0 0 0 22 29 2 0 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 31 2 0 0 0 0 24 34 1 0 0 0 0 25 2 1 6 0 0 0 26 3 1 1 0 0 0 26 33 1 0 0 0 0 27 28 1 6 0 0 0 28 32 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.26
Volume:	466.354
LogP:	4.589
LogD:	3.796
LogS:	-5.163
# Rotatable Bonds:	1
TPSA:	65.13
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.255
Synthetic Accessibility Score:	6.645
Fsp3:	0.786
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.962
MDCK Permeability:	1.6703295841580257e-05
Pgp-inhibitor:	0.333
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.439
30% Bioavailability (F30%):	0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.832
Plasma Protein Binding (PPB):	81.82659149169922%
Volume Distribution (VD):	1.237
Pgp-substrate:	12.94078540802002%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.813
CYP2C19-inhibitor:	0.327
CYP2C19-substrate:	0.871
CYP2C9-inhibitor:	0.47
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.909
CYP3A4-substrate:	0.845

ADMET: Excretion

Clearance (CL):	15.525
Half-life (T1/2):	0.162

ADMET: Toxicity

hERG Blockers:	0.829
Human Hepatotoxicity (H-HT):	0.498
Drug-inuced Liver Injury (DILI):	0.78
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.895
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.898
Carcinogencity:	0.787
Eye Corrosion:	0.093
Eye Irritation:	0.066
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: NPC470959

Natural Product ID:	NPC470959
*Common Name:**	Withametelin O
IUPAC Name:	(1R,5S,8R)-8-[(5R,6R,8S,9S,10R,13S,14S,17R)-5,6-dihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]-5-methyl-4-methylidene-2,6-dioxabicyclo[3.3.1]nonan-3-one
Synonyms:	Withametelin O
Standard InCHIKey:	QDXNBCJROMNCKV-YAZLIRBPSA-N
Standard InCHI:	InChI=1S/C28H38O6/c1-15-24(31)34-21-13-26(15,3)33-14-17(21)19-8-7-18-16-12-23(30)28(32)10-5-6-22(29)27(28,4)20(16)9-11-25(18,19)2/h5-6,16-21,23,30,32H,1,7-14H2,2-4H3/t16-,17-,18-,19+,20-,21+,23+,25-,26-,27-,28-/m0/s1
SMILES:	O=C1O[C@@H]2C[C@](C1=C)(C)OC[C@H]2[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@H]([C@@]2([C@]1(C)C(=O)C=CC2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333591
PubChem CID:	71716989
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones

*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
NPO22157	Datura wrightii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23252848]
NPO22157	Datura wrightii	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	4
Others	1

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	Ratio IC50	=	4.1	n.a.	PMID[554080]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	4600.0	nM	PMID[554080]
NPT380	Cell Line	U-251	Homo sapiens	IC50	=	2800.0	nM	PMID[554080]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3000.0	nM	PMID[554080]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1100.0	nM	PMID[554080]

☑ 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 NPC470959 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	236
0.1-0.2	1381
0.2-0.3	4175
0.3-0.4	8085
0.4-0.5	12695
0.5-0.6	6500
0.6-0.7	5693
0.7-0.8	3495
0.8-0.85	396
0.85-0.9	35
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476965
0.9727	High Similarity	NPC476961
0.9286	High Similarity	NPC476960
0.9273	High Similarity	NPC147912
0.9273	High Similarity	NPC67259
0.9174	High Similarity	NPC470960
0.9099	High Similarity	NPC470953
0.9035	High Similarity	NPC476962
0.9018	High Similarity	NPC270929
0.8966	High Similarity	NPC11895
0.8938	High Similarity	NPC286528
0.8938	High Similarity	NPC20302
0.8938	High Similarity	NPC140055
0.8938	High Similarity	NPC167606
0.8879	High Similarity	NPC170538
0.886	High Similarity	NPC329736
0.886	High Similarity	NPC257457
0.886	High Similarity	NPC50774
0.886	High Similarity	NPC311554
0.886	High Similarity	NPC709
0.885	High Similarity	NPC476963
0.8839	High Similarity	NPC122056
0.8814	High Similarity	NPC293112
0.8803	High Similarity	NPC469789
0.8783	High Similarity	NPC264954
0.8783	High Similarity	NPC61520
0.8772	High Similarity	NPC470492
0.8772	High Similarity	NPC183580
0.8772	High Similarity	NPC312824
0.8772	High Similarity	NPC470493
0.8729	High Similarity	NPC172154
0.8729	High Similarity	NPC81736
0.8729	High Similarity	NPC8369
0.8707	High Similarity	NPC474370
0.8704	High Similarity	NPC470954
0.8684	High Similarity	NPC64318
0.8661	High Similarity	NPC474315
0.8655	High Similarity	NPC473635
0.8649	High Similarity	NPC41405
0.8644	High Similarity	NPC204812
0.8632	High Similarity	NPC67569
0.8621	High Similarity	NPC473270
0.8609	High Similarity	NPC471854
0.8609	High Similarity	NPC476959
0.8596	High Similarity	NPC284915
0.8595	High Similarity	NPC476966
0.8595	High Similarity	NPC231529
0.8571	High Similarity	NPC32868
0.8571	High Similarity	NPC37116
0.8571	High Similarity	NPC241456
0.8559	High Similarity	NPC269642
0.8559	High Similarity	NPC88326
0.8559	High Similarity	NPC23786
0.8559	High Similarity	NPC470265
0.8559	High Similarity	NPC153700
0.8532	High Similarity	NPC264048
0.8509	High Similarity	NPC194273
0.8487	Intermediate Similarity	NPC473979
0.8482	Intermediate Similarity	NPC475065
0.8475	Intermediate Similarity	NPC46570
0.8468	Intermediate Similarity	NPC91034
0.8468	Intermediate Similarity	NPC475294
0.8468	Intermediate Similarity	NPC329048
0.8468	Intermediate Similarity	NPC330011
0.8468	Intermediate Similarity	NPC470952
0.8462	Intermediate Similarity	NPC473274
0.8462	Intermediate Similarity	NPC475041
0.8448	Intermediate Similarity	NPC239273
0.8448	Intermediate Similarity	NPC55296
0.8448	Intermediate Similarity	NPC134430
0.8448	Intermediate Similarity	NPC243065
0.8448	Intermediate Similarity	NPC284068
0.8435	Intermediate Similarity	NPC243354
0.843	Intermediate Similarity	NPC287423
0.843	Intermediate Similarity	NPC470882
0.8426	Intermediate Similarity	NPC316964
0.8421	Intermediate Similarity	NPC475524
0.8421	Intermediate Similarity	NPC191620
0.8421	Intermediate Similarity	NPC100267
0.8417	Intermediate Similarity	NPC3381
0.8417	Intermediate Similarity	NPC470494
0.8417	Intermediate Similarity	NPC473255
0.8417	Intermediate Similarity	NPC8374
0.8407	Intermediate Similarity	NPC29133
0.8407	Intermediate Similarity	NPC239097
0.8407	Intermediate Similarity	NPC473627
0.8403	Intermediate Similarity	NPC107493
0.8393	Intermediate Similarity	NPC177064
0.8393	Intermediate Similarity	NPC318363
0.8393	Intermediate Similarity	NPC473482
0.8393	Intermediate Similarity	NPC475418
0.8387	Intermediate Similarity	NPC316915
0.8378	Intermediate Similarity	NPC60681
0.8376	Intermediate Similarity	NPC186525
0.8376	Intermediate Similarity	NPC473720
0.8362	Intermediate Similarity	NPC44170
0.8361	Intermediate Similarity	NPC245094
0.8361	Intermediate Similarity	NPC473620
0.8348	Intermediate Similarity	NPC320118
0.8348	Intermediate Similarity	NPC255017
0.8333	Intermediate Similarity	NPC120724
0.8333	Intermediate Similarity	NPC470961
0.8333	Intermediate Similarity	NPC471243
0.8319	Intermediate Similarity	NPC214644
0.8319	Intermediate Similarity	NPC473256
0.8319	Intermediate Similarity	NPC470878
0.8306	Intermediate Similarity	NPC471855
0.8306	Intermediate Similarity	NPC231240
0.8305	Intermediate Similarity	NPC473636
0.8305	Intermediate Similarity	NPC77689
0.8305	Intermediate Similarity	NPC473203
0.8305	Intermediate Similarity	NPC475520
0.8305	Intermediate Similarity	NPC42673
0.8305	Intermediate Similarity	NPC230513
0.8304	Intermediate Similarity	NPC301666
0.8304	Intermediate Similarity	NPC473284
0.8304	Intermediate Similarity	NPC476958
0.8304	Intermediate Similarity	NPC144459
0.8291	Intermediate Similarity	NPC218970
0.8291	Intermediate Similarity	NPC475809
0.8279	Intermediate Similarity	NPC156797
0.8279	Intermediate Similarity	NPC473253
0.8279	Intermediate Similarity	NPC473265
0.8273	Intermediate Similarity	NPC185530
0.8273	Intermediate Similarity	NPC136289
0.8264	Intermediate Similarity	NPC470922
0.8264	Intermediate Similarity	NPC24651
0.8261	Intermediate Similarity	NPC269530
0.8261	Intermediate Similarity	NPC476163
0.8261	Intermediate Similarity	NPC277769
0.8261	Intermediate Similarity	NPC205534
0.8261	Intermediate Similarity	NPC476964
0.8261	Intermediate Similarity	NPC69291
0.8246	Intermediate Similarity	NPC5284
0.8241	Intermediate Similarity	NPC473456
0.8235	Intermediate Similarity	NPC79579
0.8235	Intermediate Similarity	NPC251226
0.8235	Intermediate Similarity	NPC268530
0.8235	Intermediate Similarity	NPC154491
0.823	Intermediate Similarity	NPC472825
0.8226	Intermediate Similarity	NPC173347
0.822	Intermediate Similarity	NPC153440
0.8211	Intermediate Similarity	NPC311534
0.8205	Intermediate Similarity	NPC190286
0.8205	Intermediate Similarity	NPC268954
0.8205	Intermediate Similarity	NPC148458
0.8198	Intermediate Similarity	NPC475050
0.8198	Intermediate Similarity	NPC26478
0.8198	Intermediate Similarity	NPC112009
0.8198	Intermediate Similarity	NPC476889
0.819	Intermediate Similarity	NPC250109
0.819	Intermediate Similarity	NPC962
0.819	Intermediate Similarity	NPC25909
0.819	Intermediate Similarity	NPC194100
0.8182	Intermediate Similarity	NPC265557
0.8182	Intermediate Similarity	NPC474327
0.8182	Intermediate Similarity	NPC105926
0.8182	Intermediate Similarity	NPC18945
0.8182	Intermediate Similarity	NPC67251
0.8182	Intermediate Similarity	NPC224720
0.8182	Intermediate Similarity	NPC91693
0.8182	Intermediate Similarity	NPC476223
0.8182	Intermediate Similarity	NPC81530
0.8182	Intermediate Similarity	NPC476240
0.8174	Intermediate Similarity	NPC474229
0.8174	Intermediate Similarity	NPC171888
0.8174	Intermediate Similarity	NPC146945
0.8167	Intermediate Similarity	NPC159456
0.8167	Intermediate Similarity	NPC4021
0.8167	Intermediate Similarity	NPC470921
0.8165	Intermediate Similarity	NPC114274
0.8158	Intermediate Similarity	NPC5475
0.8158	Intermediate Similarity	NPC284828
0.8158	Intermediate Similarity	NPC472216
0.8158	Intermediate Similarity	NPC173905
0.8151	Intermediate Similarity	NPC473839
0.8151	Intermediate Similarity	NPC211093
0.8151	Intermediate Similarity	NPC5292
0.8151	Intermediate Similarity	NPC476529
0.8151	Intermediate Similarity	NPC475775
0.8145	Intermediate Similarity	NPC470880
0.8145	Intermediate Similarity	NPC473593
0.8145	Intermediate Similarity	NPC471407
0.8142	Intermediate Similarity	NPC220974
0.8142	Intermediate Similarity	NPC44063
0.8136	Intermediate Similarity	NPC287343
0.8136	Intermediate Similarity	NPC97908
0.8136	Intermediate Similarity	NPC122033
0.8136	Intermediate Similarity	NPC474654
0.8136	Intermediate Similarity	NPC473968
0.8136	Intermediate Similarity	NPC470854
0.8125	Intermediate Similarity	NPC75531
0.8125	Intermediate Similarity	NPC189616
0.8125	Intermediate Similarity	NPC471293
0.8125	Intermediate Similarity	NPC149124
0.8125	Intermediate Similarity	NPC284865
0.8125	Intermediate Similarity	NPC255309
0.8125	Intermediate Similarity	NPC137657
0.812	Intermediate Similarity	NPC238667
0.812	Intermediate Similarity	NPC110861

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 NPC470959 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	1548
0.2-0.3	3643
0.3-0.4	2433
0.4-0.5	806
0.5-0.6	227
0.6-0.7	145
0.7-0.8	136
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8938	High Similarity	NPD7115	Discovery
0.823	Intermediate Similarity	NPD6899	Approved
0.823	Intermediate Similarity	NPD6881	Approved
0.8174	Intermediate Similarity	NPD6650	Approved
0.8174	Intermediate Similarity	NPD6649	Approved
0.8142	Intermediate Similarity	NPD5697	Approved
0.8103	Intermediate Similarity	NPD8297	Approved
0.8087	Intermediate Similarity	NPD6883	Approved
0.8087	Intermediate Similarity	NPD7290	Approved
0.8087	Intermediate Similarity	NPD7102	Approved
0.8053	Intermediate Similarity	NPD6675	Approved
0.8053	Intermediate Similarity	NPD6402	Approved
0.8053	Intermediate Similarity	NPD5739	Approved
0.8053	Intermediate Similarity	NPD7128	Approved
0.8017	Intermediate Similarity	NPD6847	Approved
0.8017	Intermediate Similarity	NPD6617	Approved
0.8017	Intermediate Similarity	NPD6869	Approved
0.8017	Intermediate Similarity	NPD8130	Phase 1
0.8	Intermediate Similarity	NPD6372	Approved
0.8	Intermediate Similarity	NPD6014	Approved
0.8	Intermediate Similarity	NPD6013	Approved
0.8	Intermediate Similarity	NPD6373	Approved
0.8	Intermediate Similarity	NPD6012	Approved
0.7949	Intermediate Similarity	NPD6882	Approved
0.7944	Intermediate Similarity	NPD6079	Approved
0.7934	Intermediate Similarity	NPD6319	Approved
0.7913	Intermediate Similarity	NPD6011	Approved
0.7913	Intermediate Similarity	NPD7320	Approved
0.7838	Intermediate Similarity	NPD4225	Approved
0.7826	Intermediate Similarity	NPD5701	Approved
0.7788	Intermediate Similarity	NPD5211	Phase 2
0.7778	Intermediate Similarity	NPD4634	Approved
0.7768	Intermediate Similarity	NPD5286	Approved
0.7768	Intermediate Similarity	NPD4696	Approved
0.7768	Intermediate Similarity	NPD5285	Approved
0.7759	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD5328	Approved
0.7731	Intermediate Similarity	NPD4632	Approved
0.7717	Intermediate Similarity	NPD7319	Approved
0.7706	Intermediate Similarity	NPD6399	Phase 3
0.768	Intermediate Similarity	NPD7492	Approved
0.7658	Intermediate Similarity	NPD5221	Approved
0.7658	Intermediate Similarity	NPD5222	Approved
0.7658	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD5141	Approved
0.7642	Intermediate Similarity	NPD6054	Approved
0.7638	Intermediate Similarity	NPD7736	Approved
0.7636	Intermediate Similarity	NPD7748	Approved
0.7632	Intermediate Similarity	NPD5225	Approved
0.7632	Intermediate Similarity	NPD4633	Approved
0.7632	Intermediate Similarity	NPD5226	Approved
0.7632	Intermediate Similarity	NPD5224	Approved
0.7619	Intermediate Similarity	NPD7507	Approved
0.7619	Intermediate Similarity	NPD6616	Approved
0.7615	Intermediate Similarity	NPD7515	Phase 2
0.76	Intermediate Similarity	NPD8328	Phase 3
0.7589	Intermediate Similarity	NPD6084	Phase 2
0.7589	Intermediate Similarity	NPD5173	Approved
0.7589	Intermediate Similarity	NPD7902	Approved
0.7589	Intermediate Similarity	NPD6083	Phase 2
0.7589	Intermediate Similarity	NPD4755	Approved
0.757	Intermediate Similarity	NPD3573	Approved
0.7565	Intermediate Similarity	NPD5175	Approved
0.7565	Intermediate Similarity	NPD5174	Approved
0.7563	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7101	Approved
0.7561	Intermediate Similarity	NPD7100	Approved
0.7559	Intermediate Similarity	NPD7078	Approved
0.7544	Intermediate Similarity	NPD5223	Approved
0.7522	Intermediate Similarity	NPD7638	Approved
0.752	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD4697	Phase 3
0.748	Intermediate Similarity	NPD6335	Approved
0.7477	Intermediate Similarity	NPD3618	Phase 1
0.7459	Intermediate Similarity	NPD6274	Approved
0.7459	Intermediate Similarity	NPD6868	Approved
0.7456	Intermediate Similarity	NPD7639	Approved
0.7456	Intermediate Similarity	NPD4700	Approved
0.7456	Intermediate Similarity	NPD7640	Approved
0.7455	Intermediate Similarity	NPD6411	Approved
0.744	Intermediate Similarity	NPD6015	Approved
0.744	Intermediate Similarity	NPD6016	Approved
0.7436	Intermediate Similarity	NPD6008	Approved
0.7398	Intermediate Similarity	NPD6009	Approved
0.7398	Intermediate Similarity	NPD6317	Approved
0.7381	Intermediate Similarity	NPD5988	Approved
0.7368	Intermediate Similarity	NPD5696	Approved
0.736	Intermediate Similarity	NPD6059	Approved
0.7339	Intermediate Similarity	NPD6314	Approved
0.7339	Intermediate Similarity	NPD6313	Approved
0.7323	Intermediate Similarity	NPD7604	Phase 2
0.7321	Intermediate Similarity	NPD7900	Approved
0.7321	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD4730	Approved
0.7311	Intermediate Similarity	NPD4729	Approved
0.7302	Intermediate Similarity	NPD8515	Approved
0.7302	Intermediate Similarity	NPD5983	Phase 2
0.7302	Intermediate Similarity	NPD8033	Approved
0.7302	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD8513	Phase 3
0.7302	Intermediate Similarity	NPD7503	Approved
0.7302	Intermediate Similarity	NPD8516	Approved
0.7302	Intermediate Similarity	NPD8517	Approved
0.729	Intermediate Similarity	NPD4786	Approved
0.7287	Intermediate Similarity	NPD8293	Discontinued
0.7273	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6101	Approved
0.7258	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5695	Phase 3
0.7257	Intermediate Similarity	NPD4629	Approved
0.7257	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5210	Approved
0.725	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4202	Approved
0.7227	Intermediate Similarity	NPD6412	Phase 2
0.7222	Intermediate Similarity	NPD8377	Approved
0.7222	Intermediate Similarity	NPD8294	Approved
0.7209	Intermediate Similarity	NPD6336	Discontinued
0.7207	Intermediate Similarity	NPD5785	Approved
0.719	Intermediate Similarity	NPD5249	Phase 3
0.719	Intermediate Similarity	NPD5251	Approved
0.719	Intermediate Similarity	NPD5250	Approved
0.719	Intermediate Similarity	NPD5248	Approved
0.719	Intermediate Similarity	NPD5247	Approved
0.7182	Intermediate Similarity	NPD5737	Approved
0.7182	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6672	Approved
0.7167	Intermediate Similarity	NPD6686	Approved
0.7167	Intermediate Similarity	NPD5128	Approved
0.7165	Intermediate Similarity	NPD8296	Approved
0.7165	Intermediate Similarity	NPD6908	Approved
0.7165	Intermediate Similarity	NPD8380	Approved
0.7165	Intermediate Similarity	NPD8335	Approved
0.7165	Intermediate Similarity	NPD6909	Approved
0.7165	Intermediate Similarity	NPD8379	Approved
0.7165	Intermediate Similarity	NPD8378	Approved
0.7156	Intermediate Similarity	NPD7521	Approved
0.7156	Intermediate Similarity	NPD7146	Approved
0.7156	Intermediate Similarity	NPD7334	Approved
0.7156	Intermediate Similarity	NPD6409	Approved
0.7156	Intermediate Similarity	NPD6684	Approved
0.7156	Intermediate Similarity	NPD5330	Approved
0.7154	Intermediate Similarity	NPD8133	Approved
0.7143	Intermediate Similarity	NPD4767	Approved
0.7143	Intermediate Similarity	NPD8034	Phase 2
0.7143	Intermediate Similarity	NPD4768	Approved
0.7143	Intermediate Similarity	NPD7516	Approved
0.7143	Intermediate Similarity	NPD5693	Phase 1
0.7143	Intermediate Similarity	NPD8035	Phase 2
0.7131	Intermediate Similarity	NPD5215	Approved
0.7131	Intermediate Similarity	NPD5217	Approved
0.7131	Intermediate Similarity	NPD5216	Approved
0.7119	Intermediate Similarity	NPD4754	Approved
0.7117	Intermediate Similarity	NPD4753	Phase 2
0.7107	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3667	Approved
0.7073	Intermediate Similarity	NPD6053	Discontinued
0.7064	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD1694	Approved
0.7063	Intermediate Similarity	NPD7328	Approved
0.7063	Intermediate Similarity	NPD7327	Approved
0.7049	Intermediate Similarity	NPD5135	Approved
0.7049	Intermediate Similarity	NPD5169	Approved
0.7049	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6921	Approved
0.7027	Intermediate Similarity	NPD6903	Approved
0.7025	Intermediate Similarity	NPD5168	Approved
0.6992	Remote Similarity	NPD5127	Approved
0.6991	Remote Similarity	NPD5281	Approved
0.6991	Remote Similarity	NPD5284	Approved
0.6972	Remote Similarity	NPD3666	Approved
0.6972	Remote Similarity	NPD3133	Approved
0.6972	Remote Similarity	NPD3665	Phase 1
0.6964	Remote Similarity	NPD6080	Approved
0.6964	Remote Similarity	NPD6904	Approved
0.6964	Remote Similarity	NPD6673	Approved
0.693	Remote Similarity	NPD5779	Approved
0.693	Remote Similarity	NPD5778	Approved
0.6911	Remote Similarity	NPD6371	Approved
0.6891	Remote Similarity	NPD7632	Discontinued
0.687	Remote Similarity	NPD6001	Approved
0.6842	Remote Similarity	NPD6033	Approved
0.6842	Remote Similarity	NPD7637	Suspended
0.6825	Remote Similarity	NPD5167	Approved
0.6815	Remote Similarity	NPD7260	Phase 2
0.6803	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4221	Approved
0.6789	Remote Similarity	NPD4223	Phase 3
0.6789	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD8074	Phase 3
0.6759	Remote Similarity	NPD7236	Approved
0.6757	Remote Similarity	NPD5363	Approved
0.6757	Remote Similarity	NPD5329	Approved
0.6754	Remote Similarity	NPD5207	Approved
0.6726	Remote Similarity	NPD5208	Approved
0.6697	Remote Similarity	NPD5369	Approved
0.6696	Remote Similarity	NPD5694	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