NPASS Compound

Structure

CID61520 OpenBabel06191715402D 35 40 0 0 1 0 0 0 0 0999 V2000 -6.6987 -2.3641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9757 -3.7823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4818 -4.3292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5074 -5.7076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6533 -1.9104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6533 -0.9552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8273 -3.3425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6545 -3.8201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4706 -3.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6545 -0.9552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1351 -2.3879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4039 -3.2716 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0424 -3.9807 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6545 -1.9103 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8273 -2.3879 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4817 -2.3879 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1351 -3.3425 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8266 -2.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8267 -0.4776 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1757 -4.3775 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8272 -0.4776 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3090 -3.8201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7475 -4.8882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4818 -3.3425 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.9104 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3090 -4.7743 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9552 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9897 -3.8356 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8266 -3.3747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8267 0.5091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3860 -5.5973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5999 -5.4128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8142 -5.0866 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 4 26 1 0 0 0 0 6 7 2 0 0 0 0 6 19 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 25 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 1 1 1 0 0 0 13 14 1 0 0 0 0 14 2 1 6 0 0 0 14 24 1 0 0 0 0 15 11 1 6 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 26 1 1 0 0 0 17 25 1 1 0 0 0 18 23 1 0 0 0 0 18 29 1 1 0 0 0 19 26 1 0 0 0 0 19 30 2 0 0 0 0 20 28 1 1 0 0 0 20 31 1 0 0 0 0 21 27 1 6 0 0 0 21 34 1 0 0 0 0 22 28 1 1 0 0 0 22 35 1 0 0 0 0 23 25 1 1 0 0 0 23 27 1 0 0 0 0 24 32 2 0 0 0 0 24 34 1 0 0 0 0 25 3 1 1 0 0 0 26 28 1 1 0 0 0 27 5 1 6 0 0 0 27 33 1 0 0 0 0 28 35 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.28
Volume:	495.128
LogP:	3.153
LogD:	3.172
LogS:	-4.566
# Rotatable Bonds:	2
TPSA:	113.43
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.454
Synthetic Accessibility Score:	6.122
Fsp3:	0.893
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:	-5.184
MDCK Permeability:	4.230854756315239e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.122
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.861
Plasma Protein Binding (PPB):	49.57227325439453%
Volume Distribution (VD):	0.581
Pgp-substrate:	35.737213134765625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.777
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.832
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.668
CYP3A4-substrate:	0.698

ADMET: Excretion

Clearance (CL):	10.662
Half-life (T1/2):	0.771

ADMET: Toxicity

hERG Blockers:	0.548
Human Hepatotoxicity (H-HT):	0.453
Drug-inuced Liver Injury (DILI):	0.294
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.58
Maximum Recommended Daily Dose:	0.451
Skin Sensitization:	0.49
Carcinogencity:	0.606
Eye Corrosion:	0.027
Eye Irritation:	0.03
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC61520

Natural Product ID:	NPC61520
*Common Name:**	Withaphysacarpin
IUPAC Name:	n.a.
Synonyms:	Withaphysacarpin
Standard InCHIKey:	CZKZWDJWVZTWCF-KUQCCCELSA-N
Standard InCHI:	InChI=1S/C28H40O7/c1-13-10-21(34-24(32)14(13)2)27(5,33)23-18(29)12-17-15-11-22-28(35-22)20(31)7-6-19(30)26(28,4)16(15)8-9-25(17,23)3/h6-7,13-18,20-23,29,31,33H,8-12H2,1-5H3/t13-,14+,15+,16-,17-,18-,20-,21+,22+,23-,25-,26-,27-,28+/m0/s1
SMILES:	C[C@H]1C[C@H]([C@@](C)([C@H]2[C@H](C[C@H]3[C@@H]4C[C@@H]5[C@@]6([C@H](C=CC(=O)[C@]6(C)[C@H]4CC[C@]23C)O)O5)O)O)OC(=O)[C@@H]1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452952
PubChem CID:	44567005
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
NPO13655	Physalis philadelphica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO13655	Physalis philadelphica	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO13655	Physalis philadelphica	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13655	Physalis philadelphica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13655	Physalis philadelphica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13655	Physalis philadelphica	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	4

Activity Type	# Activity
Individual Protein	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CQ	=	1.9	uM	PMID[458189]
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	0.43	uM	PMID[458189]
NPT27	Others	Unspecified		IC50	=	4800.0	nM	PMID[458189]
NPT2	Others	Unspecified		Ratio	=	11.1	n.a.	PMID[458189]
NPT2	Others	Unspecified		Ratio	=	2.5	n.a.	PMID[458189]

☑ 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 NPC61520 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	247
0.1-0.2	1436
0.2-0.3	4379
0.3-0.4	8487
0.4-0.5	12336
0.5-0.6	6545
0.6-0.7	6132
0.7-0.8	2813
0.8-0.85	231
0.85-0.9	76
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9908	High Similarity	NPC329736
0.9725	High Similarity	NPC270929
0.9397	High Similarity	NPC473253
0.9381	High Similarity	NPC474370
0.9292	High Similarity	NPC264954
0.9237	High Similarity	NPC470880
0.9217	High Similarity	NPC153700
0.9217	High Similarity	NPC88326
0.9204	High Similarity	NPC709
0.9204	High Similarity	NPC50774
0.9138	High Similarity	NPC469789
0.9123	High Similarity	NPC473203
0.9115	High Similarity	NPC140055
0.9115	High Similarity	NPC286528
0.9115	High Similarity	NPC20302
0.9115	High Similarity	NPC470492
0.9115	High Similarity	NPC167606
0.9068	High Similarity	NPC470882
0.9068	High Similarity	NPC473265
0.906	High Similarity	NPC8374
0.8983	High Similarity	NPC293112
0.8966	High Similarity	NPC67569
0.8947	High Similarity	NPC470493
0.8947	High Similarity	NPC312824
0.8947	High Similarity	NPC183580
0.8908	High Similarity	NPC287423
0.8898	High Similarity	NPC81736
0.8898	High Similarity	NPC8369
0.8898	High Similarity	NPC172154
0.8889	High Similarity	NPC23786
0.8889	High Similarity	NPC470265
0.887	High Similarity	NPC186525
0.885	High Similarity	NPC122056
0.8814	High Similarity	NPC11895
0.8803	High Similarity	NPC470878
0.8803	High Similarity	NPC473256
0.8803	High Similarity	NPC46570
0.8783	High Similarity	NPC470959
0.8783	High Similarity	NPC476965
0.8783	High Similarity	NPC471854
0.8772	High Similarity	NPC147912
0.8772	High Similarity	NPC67259
0.8739	High Similarity	NPC473255
0.8729	High Similarity	NPC269642
0.8729	High Similarity	NPC170538
0.8729	High Similarity	NPC107493
0.8684	High Similarity	NPC250109
0.8684	High Similarity	NPC317210
0.8678	High Similarity	NPC473620
0.8667	High Similarity	NPC473635
0.8661	High Similarity	NPC41405
0.8661	High Similarity	NPC475941
0.8661	High Similarity	NPC474901
0.8655	High Similarity	NPC204812
0.8636	High Similarity	NPC149124
0.8636	High Similarity	NPC75531
0.8632	High Similarity	NPC473274
0.8632	High Similarity	NPC475041
0.8632	High Similarity	NPC476960
0.8609	High Similarity	NPC284915
0.8607	High Similarity	NPC231529
0.8596	High Similarity	NPC476163
0.8596	High Similarity	NPC475970
0.8596	High Similarity	NPC191620
0.8595	High Similarity	NPC305496
0.8583	High Similarity	NPC32868
0.8583	High Similarity	NPC3381
0.8583	High Similarity	NPC241456
0.8583	High Similarity	NPC470494
0.8559	High Similarity	NPC476961
0.8547	High Similarity	NPC257457
0.8547	High Similarity	NPC473720
0.8547	High Similarity	NPC311554
0.8534	High Similarity	NPC64318
0.8525	High Similarity	NPC473888
0.8522	High Similarity	NPC962
0.8509	High Similarity	NPC470960
0.85	High Similarity	NPC473979
0.8496	Intermediate Similarity	NPC214644
0.8482	Intermediate Similarity	NPC144459
0.8475	Intermediate Similarity	NPC473270
0.8468	Intermediate Similarity	NPC231240
0.8462	Intermediate Similarity	NPC243065
0.8462	Intermediate Similarity	NPC218970
0.8455	Intermediate Similarity	NPC136289
0.8455	Intermediate Similarity	NPC473593
0.8448	Intermediate Similarity	NPC243354
0.8435	Intermediate Similarity	NPC207251
0.8421	Intermediate Similarity	NPC37116
0.8421	Intermediate Similarity	NPC76084
0.8403	Intermediate Similarity	NPC79579
0.8403	Intermediate Similarity	NPC476962
0.8403	Intermediate Similarity	NPC268530
0.8403	Intermediate Similarity	NPC154491
0.84	Intermediate Similarity	NPC316915
0.839	Intermediate Similarity	NPC153440
0.8376	Intermediate Similarity	NPC49492
0.8376	Intermediate Similarity	NPC266728
0.8376	Intermediate Similarity	NPC190286
0.8376	Intermediate Similarity	NPC298278
0.8374	Intermediate Similarity	NPC311534
0.8364	Intermediate Similarity	NPC224720
0.8364	Intermediate Similarity	NPC81530
0.8364	Intermediate Similarity	NPC476240
0.8364	Intermediate Similarity	NPC476223
0.8362	Intermediate Similarity	NPC194100
0.8362	Intermediate Similarity	NPC255017
0.8348	Intermediate Similarity	NPC470961
0.8348	Intermediate Similarity	NPC474315
0.8347	Intermediate Similarity	NPC120724
0.8333	Intermediate Similarity	NPC4021
0.8333	Intermediate Similarity	NPC159456
0.832	Intermediate Similarity	NPC471855
0.8319	Intermediate Similarity	NPC475060
0.8319	Intermediate Similarity	NPC83744
0.8319	Intermediate Similarity	NPC475520
0.8319	Intermediate Similarity	NPC44063
0.8319	Intermediate Similarity	NPC473284
0.8319	Intermediate Similarity	NPC5292
0.8319	Intermediate Similarity	NPC220229
0.8305	Intermediate Similarity	NPC239273
0.8291	Intermediate Similarity	NPC326542
0.8288	Intermediate Similarity	NPC477915
0.8288	Intermediate Similarity	NPC473424
0.8279	Intermediate Similarity	NPC469790
0.8276	Intermediate Similarity	NPC71348
0.8276	Intermediate Similarity	NPC100267
0.8276	Intermediate Similarity	NPC475524
0.8276	Intermediate Similarity	NPC269530
0.8273	Intermediate Similarity	NPC476274
0.8264	Intermediate Similarity	NPC28532
0.8264	Intermediate Similarity	NPC222688
0.8261	Intermediate Similarity	NPC197428
0.8261	Intermediate Similarity	NPC29133
0.825	Intermediate Similarity	NPC251226
0.825	Intermediate Similarity	NPC474585
0.8246	Intermediate Similarity	NPC65941
0.8246	Intermediate Similarity	NPC329417
0.8246	Intermediate Similarity	NPC217201
0.8246	Intermediate Similarity	NPC177064
0.824	Intermediate Similarity	NPC173347
0.8235	Intermediate Similarity	NPC251310
0.8231	Intermediate Similarity	NPC473396
0.823	Intermediate Similarity	NPC97202
0.823	Intermediate Similarity	NPC214264
0.823	Intermediate Similarity	NPC85829
0.823	Intermediate Similarity	NPC302607
0.823	Intermediate Similarity	NPC60681
0.823	Intermediate Similarity	NPC48733
0.823	Intermediate Similarity	NPC49958
0.823	Intermediate Similarity	NPC296945
0.823	Intermediate Similarity	NPC150531
0.823	Intermediate Similarity	NPC260268
0.823	Intermediate Similarity	NPC50692
0.823	Intermediate Similarity	NPC149047
0.823	Intermediate Similarity	NPC202167
0.823	Intermediate Similarity	NPC319077
0.823	Intermediate Similarity	NPC476027
0.823	Intermediate Similarity	NPC152695
0.823	Intermediate Similarity	NPC171137
0.822	Intermediate Similarity	NPC148458
0.822	Intermediate Similarity	NPC176840
0.8217	Intermediate Similarity	NPC473233
0.8214	Intermediate Similarity	NPC311612
0.8214	Intermediate Similarity	NPC264048
0.8214	Intermediate Similarity	NPC475050
0.8214	Intermediate Similarity	NPC26478
0.8214	Intermediate Similarity	NPC236390
0.8211	Intermediate Similarity	NPC159499
0.8211	Intermediate Similarity	NPC174367
0.8211	Intermediate Similarity	NPC47113
0.8205	Intermediate Similarity	NPC194273
0.8198	Intermediate Similarity	NPC476897
0.819	Intermediate Similarity	NPC471243
0.819	Intermediate Similarity	NPC474229
0.8182	Intermediate Similarity	NPC202051
0.8182	Intermediate Similarity	NPC310511
0.8182	Intermediate Similarity	NPC470921
0.8174	Intermediate Similarity	NPC2766
0.8174	Intermediate Similarity	NPC87335
0.8174	Intermediate Similarity	NPC11710
0.8174	Intermediate Similarity	NPC475065
0.8167	Intermediate Similarity	NPC42673
0.8167	Intermediate Similarity	NPC305260
0.8167	Intermediate Similarity	NPC270850
0.816	Intermediate Similarity	NPC471407
0.816	Intermediate Similarity	NPC476966
0.8158	Intermediate Similarity	NPC330011
0.8158	Intermediate Similarity	NPC471783
0.8158	Intermediate Similarity	NPC473165
0.8158	Intermediate Similarity	NPC9457
0.8158	Intermediate Similarity	NPC185
0.8158	Intermediate Similarity	NPC477916
0.8158	Intermediate Similarity	NPC91034
0.8158	Intermediate Similarity	NPC329048
0.8158	Intermediate Similarity	NPC220974
0.8151	Intermediate Similarity	NPC55296
0.8151	Intermediate Similarity	NPC470171
0.8151	Intermediate Similarity	NPC469684
0.8145	Intermediate Similarity	NPC42399

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 NPC61520 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	1624
0.2-0.3	3770
0.3-0.4	2343
0.4-0.5	697
0.5-0.6	214
0.6-0.7	163
0.7-0.8	114
0.8-0.85	14
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9115	High Similarity	NPD7115	Discovery
0.8435	Intermediate Similarity	NPD8297	Approved
0.8407	Intermediate Similarity	NPD6899	Approved
0.8407	Intermediate Similarity	NPD6881	Approved
0.8348	Intermediate Similarity	NPD6650	Approved
0.8348	Intermediate Similarity	NPD6649	Approved
0.8319	Intermediate Similarity	NPD5697	Approved
0.8261	Intermediate Similarity	NPD7290	Approved
0.8261	Intermediate Similarity	NPD7102	Approved
0.8261	Intermediate Similarity	NPD6883	Approved
0.825	Intermediate Similarity	NPD6319	Approved
0.823	Intermediate Similarity	NPD6402	Approved
0.823	Intermediate Similarity	NPD6675	Approved
0.823	Intermediate Similarity	NPD5739	Approved
0.823	Intermediate Similarity	NPD7128	Approved
0.819	Intermediate Similarity	NPD6847	Approved
0.819	Intermediate Similarity	NPD6617	Approved
0.819	Intermediate Similarity	NPD8130	Phase 1
0.819	Intermediate Similarity	NPD6869	Approved
0.8174	Intermediate Similarity	NPD6012	Approved
0.8174	Intermediate Similarity	NPD6372	Approved
0.8174	Intermediate Similarity	NPD6013	Approved
0.8174	Intermediate Similarity	NPD6014	Approved
0.8174	Intermediate Similarity	NPD6373	Approved
0.8125	Intermediate Similarity	NPD5211	Phase 2
0.812	Intermediate Similarity	NPD6882	Approved
0.8087	Intermediate Similarity	NPD6011	Approved
0.8087	Intermediate Similarity	NPD7320	Approved
0.8051	Intermediate Similarity	NPD4632	Approved
0.8	Intermediate Similarity	NPD5701	Approved
0.7984	Intermediate Similarity	NPD7492	Approved
0.7982	Intermediate Similarity	NPD5141	Approved
0.7951	Intermediate Similarity	NPD6054	Approved
0.7949	Intermediate Similarity	NPD4634	Approved
0.7946	Intermediate Similarity	NPD4696	Approved
0.7946	Intermediate Similarity	NPD5285	Approved
0.7946	Intermediate Similarity	NPD5286	Approved
0.7937	Intermediate Similarity	NPD7736	Approved
0.792	Intermediate Similarity	NPD6616	Approved
0.7913	Intermediate Similarity	NPD6008	Approved
0.7874	Intermediate Similarity	NPD7319	Approved
0.7857	Intermediate Similarity	NPD7078	Approved
0.7823	Intermediate Similarity	NPD6370	Approved
0.7807	Intermediate Similarity	NPD5225	Approved
0.7807	Intermediate Similarity	NPD4633	Approved
0.7807	Intermediate Similarity	NPD5224	Approved
0.7807	Intermediate Similarity	NPD5226	Approved
0.7778	Intermediate Similarity	NPD7507	Approved
0.7768	Intermediate Similarity	NPD4755	Approved
0.776	Intermediate Similarity	NPD7604	Phase 2
0.7742	Intermediate Similarity	NPD6015	Approved
0.7742	Intermediate Similarity	NPD6016	Approved
0.7739	Intermediate Similarity	NPD5174	Approved
0.7739	Intermediate Similarity	NPD5175	Approved
0.7731	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD7100	Approved
0.7724	Intermediate Similarity	NPD7101	Approved
0.7719	Intermediate Similarity	NPD5223	Approved
0.7705	Intermediate Similarity	NPD6009	Approved
0.7699	Intermediate Similarity	NPD4225	Approved
0.768	Intermediate Similarity	NPD5988	Approved
0.7661	Intermediate Similarity	NPD6059	Approved
0.7642	Intermediate Similarity	NPD6335	Approved
0.7636	Intermediate Similarity	NPD6079	Approved
0.7632	Intermediate Similarity	NPD4700	Approved
0.7623	Intermediate Similarity	NPD6274	Approved
0.7611	Intermediate Similarity	NPD6083	Phase 2
0.7611	Intermediate Similarity	NPD6084	Phase 2
0.76	Intermediate Similarity	NPD5983	Phase 2
0.7578	Intermediate Similarity	NPD8293	Discontinued
0.7568	Intermediate Similarity	NPD6399	Phase 3
0.7561	Intermediate Similarity	NPD6317	Approved
0.7542	Intermediate Similarity	NPD6412	Phase 2
0.75	Intermediate Similarity	NPD6313	Approved
0.75	Intermediate Similarity	NPD6336	Discontinued
0.75	Intermediate Similarity	NPD6314	Approved
0.7479	Intermediate Similarity	NPD4729	Approved
0.7479	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD4730	Approved
0.746	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5328	Approved
0.7434	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD4202	Approved
0.7391	Intermediate Similarity	NPD5696	Approved
0.7387	Intermediate Similarity	NPD5785	Approved
0.7368	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5221	Approved
0.7368	Intermediate Similarity	NPD5222	Approved
0.7355	Intermediate Similarity	NPD5250	Approved
0.7355	Intermediate Similarity	NPD5248	Approved
0.7355	Intermediate Similarity	NPD5249	Phase 3
0.7355	Intermediate Similarity	NPD5251	Approved
0.7355	Intermediate Similarity	NPD5247	Approved
0.7355	Intermediate Similarity	NPD6371	Approved
0.7344	Intermediate Similarity	NPD8328	Phase 3
0.7333	Intermediate Similarity	NPD5128	Approved
0.7328	Intermediate Similarity	NPD7639	Approved
0.7328	Intermediate Similarity	NPD7640	Approved
0.7323	Intermediate Similarity	NPD7503	Approved
0.7323	Intermediate Similarity	NPD6908	Approved
0.7323	Intermediate Similarity	NPD6909	Approved
0.7311	Intermediate Similarity	NPD4768	Approved
0.7311	Intermediate Similarity	NPD4767	Approved
0.7304	Intermediate Similarity	NPD7902	Approved
0.7304	Intermediate Similarity	NPD5173	Approved
0.7295	Intermediate Similarity	NPD5217	Approved
0.7295	Intermediate Similarity	NPD5216	Approved
0.7295	Intermediate Similarity	NPD5215	Approved
0.7288	Intermediate Similarity	NPD4754	Approved
0.7281	Intermediate Similarity	NPD5695	Phase 3
0.7281	Intermediate Similarity	NPD5210	Approved
0.7281	Intermediate Similarity	NPD4629	Approved
0.7273	Intermediate Similarity	NPD3573	Approved
0.7273	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5363	Approved
0.7241	Intermediate Similarity	NPD7638	Approved
0.7222	Intermediate Similarity	NPD7327	Approved
0.7222	Intermediate Similarity	NPD7328	Approved
0.7217	Intermediate Similarity	NPD4697	Phase 3
0.7213	Intermediate Similarity	NPD5135	Approved
0.7213	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD5169	Approved
0.7207	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6868	Approved
0.7193	Intermediate Similarity	NPD7748	Approved
0.7188	Intermediate Similarity	NPD8033	Approved
0.7182	Intermediate Similarity	NPD6409	Approved
0.7182	Intermediate Similarity	NPD7521	Approved
0.7182	Intermediate Similarity	NPD7334	Approved
0.7182	Intermediate Similarity	NPD3618	Phase 1
0.7182	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6684	Approved
0.7182	Intermediate Similarity	NPD7146	Approved
0.7182	Intermediate Similarity	NPD5786	Approved
0.7182	Intermediate Similarity	NPD5330	Approved
0.7168	Intermediate Similarity	NPD5284	Approved
0.7168	Intermediate Similarity	NPD6411	Approved
0.7168	Intermediate Similarity	NPD5281	Approved
0.7168	Intermediate Similarity	NPD7515	Phase 2
0.7165	Intermediate Similarity	NPD7516	Approved
0.7154	Intermediate Similarity	NPD5127	Approved
0.7143	Intermediate Similarity	NPD4753	Phase 2
0.7121	Intermediate Similarity	NPD6033	Approved
0.7109	Intermediate Similarity	NPD8377	Approved
0.7109	Intermediate Similarity	NPD8294	Approved
0.7097	Intermediate Similarity	NPD6053	Discontinued
0.7073	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD8513	Phase 3
0.7054	Intermediate Similarity	NPD8516	Approved
0.7054	Intermediate Similarity	NPD8378	Approved
0.7054	Intermediate Similarity	NPD8517	Approved
0.7054	Intermediate Similarity	NPD8380	Approved
0.7054	Intermediate Similarity	NPD8335	Approved
0.7054	Intermediate Similarity	NPD8515	Approved
0.7054	Intermediate Similarity	NPD8379	Approved
0.7054	Intermediate Similarity	NPD6903	Approved
0.7054	Intermediate Similarity	NPD8296	Approved
0.7049	Intermediate Similarity	NPD6686	Approved
0.7043	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6001	Approved
0.7043	Intermediate Similarity	NPD7900	Approved
0.7018	Intermediate Similarity	NPD8035	Phase 2
0.7018	Intermediate Similarity	NPD8034	Phase 2
0.7008	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3665	Phase 1
0.7	Intermediate Similarity	NPD3666	Approved
0.7	Intermediate Similarity	NPD4786	Approved
0.7	Intermediate Similarity	NPD3133	Approved
0.6991	Remote Similarity	NPD6080	Approved
0.6991	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6101	Approved
0.6991	Remote Similarity	NPD6673	Approved
0.6991	Remote Similarity	NPD6904	Approved
0.6984	Remote Similarity	NPD5167	Approved
0.6972	Remote Similarity	NPD4269	Approved
0.6972	Remote Similarity	NPD4270	Approved
0.6957	Remote Similarity	NPD5779	Approved
0.6957	Remote Similarity	NPD5778	Approved
0.6903	Remote Similarity	NPD5737	Approved
0.6903	Remote Similarity	NPD6672	Approved
0.6881	Remote Similarity	NPD5369	Approved
0.687	Remote Similarity	NPD7637	Suspended
0.687	Remote Similarity	NPD5693	Phase 1
0.6855	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5344	Discontinued
0.6829	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3667	Approved
0.6818	Remote Similarity	NPD4223	Phase 3
0.6818	Remote Similarity	NPD6435	Approved
0.6818	Remote Similarity	NPD4221	Approved
0.6794	Remote Similarity	NPD6921	Approved
0.6789	Remote Similarity	NPD4252	Approved
0.6786	Remote Similarity	NPD5329	Approved
0.6786	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5207	Approved
0.6781	Remote Similarity	NPD7236	Approved
0.6777	Remote Similarity	NPD7632	Discontinued
0.6774	Remote Similarity	NPD5168	Approved
0.6772	Remote Similarity	NPD8133	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