NPASS Compound

Structure

CID321690 OpenBabel06191716162D 35 38 0 0 1 0 0 0 0 0999 V2000 -6.5446 4.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9047 3.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6176 1.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3230 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5665 4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2793 3.4190 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 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 -2.6831 -0.3090 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 1.0000 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 -5.9266 2.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2574 3.6270 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 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 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 21 2 0 0 0 0 3 21 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 7 29 1 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 0 0 0 0 16 30 1 0 0 0 0 17 31 1 0 0 0 0 18 19 1 0 0 0 0 18 29 1 0 0 0 0 20 31 1 0 0 0 0 20 32 1 0 0 0 0 21 23 1 0 0 0 0 22 4 1 1 0 0 0 22 24 1 0 0 0 0 24 29 1 6 0 0 0 25 28 1 0 0 0 0 25 31 1 6 0 0 0 26 30 1 1 0 0 0 26 32 1 0 0 0 0 27 33 2 0 0 0 0 27 34 1 0 0 0 0 28 35 1 0 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 31 32 1 1 0 0 0 32 19 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.41
Volume:	548.9
LogP:	7.273
LogD:	5.355
LogS:	-4.823
# Rotatable Bonds:	10
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.306
Synthetic Accessibility Score:	5.464
Fsp3:	0.906
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.273
MDCK Permeability:	1.1763100701500662e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.283
30% Bioavailability (F30%):	0.919

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	97.74028778076172%
Volume Distribution (VD):	0.86
Pgp-substrate:	2.23431396484375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.36
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.912
CYP2C9-inhibitor:	0.193
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.46
CYP3A4-inhibitor:	0.567
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	3.025
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.451
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.267
Skin Sensitization:	0.887
Carcinogencity:	0.172
Eye Corrosion:	0.015
Eye Irritation:	0.089
Respiratory Toxicity:	0.868

Download Data

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

Natural Product: NPC321690

Natural Product ID:	NPC321690
*Common Name:**	Metaseglyptorin A
IUPAC Name:	n.a.
Synonyms:	Metaseglyptorin A
Standard InCHIKey:	XKNFVOLVUYNREE-JEWLOWAJSA-N
Standard InCHI:	InChI=1S/C32H54O3/c1-9-23(21(2)3)11-10-22(4)24-14-16-30(8)26-13-12-25(28(5,6)35)31(17-15-27(33)34)20-32(26,31)19-18-29(24,30)7/h22-26,35H,2,9-20H2,1,3-8H3,(H,33,34)/t22-,23?,24-,25+,26+,29-,30+,31-,32+/m1/s1
SMILES:	CCC(CCC(C)C1CCC2(C1(CCC34C2CCC(C3(C4)CCC(=O)O)C(C)(C)O)C)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689205
PubChem CID:	51040263
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21226514]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	stem	n.a.	PMID[21226514]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21226514]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[572121]

☑ 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 NPC321690 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	155
0.1-0.2	1691
0.2-0.3	11042
0.3-0.4	12851
0.4-0.5	5929
0.5-0.6	6798
0.6-0.7	3492
0.7-0.8	667
0.8-0.85	47
0.85-0.9	20
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9452	High Similarity	NPC20466
0.9324	High Similarity	NPC66105
0.9079	High Similarity	NPC158846
0.8933	High Similarity	NPC246445
0.8846	High Similarity	NPC232625
0.8831	High Similarity	NPC192744
0.8816	High Similarity	NPC68828
0.8784	High Similarity	NPC161187
0.8784	High Similarity	NPC330659
0.8784	High Similarity	NPC244708
0.8765	High Similarity	NPC475007
0.8608	High Similarity	NPC147066
0.859	High Similarity	NPC477371
0.8571	High Similarity	NPC212661
0.8571	High Similarity	NPC471035
0.8554	High Similarity	NPC117122
0.8537	High Similarity	NPC70661
0.8519	High Similarity	NPC194937
0.8519	High Similarity	NPC476038
0.8493	Intermediate Similarity	NPC290445
0.8493	Intermediate Similarity	NPC36616
0.8421	Intermediate Similarity	NPC18819
0.8421	Intermediate Similarity	NPC46610
0.8415	Intermediate Similarity	NPC283733
0.8415	Intermediate Similarity	NPC269638
0.8395	Intermediate Similarity	NPC245866
0.8395	Intermediate Similarity	NPC472740
0.8395	Intermediate Similarity	NPC477373
0.8375	Intermediate Similarity	NPC38350
0.8375	Intermediate Similarity	NPC201912
0.8375	Intermediate Similarity	NPC477372
0.8354	Intermediate Similarity	NPC215843
0.8354	Intermediate Similarity	NPC118987
0.8333	Intermediate Similarity	NPC238227
0.8333	Intermediate Similarity	NPC146937
0.8313	Intermediate Similarity	NPC186975
0.8289	Intermediate Similarity	NPC279241
0.8289	Intermediate Similarity	NPC36310
0.8272	Intermediate Similarity	NPC477858
0.8272	Intermediate Similarity	NPC133391
0.8272	Intermediate Similarity	NPC260956
0.8272	Intermediate Similarity	NPC320514
0.8267	Intermediate Similarity	NPC91369
0.825	Intermediate Similarity	NPC170038
0.8235	Intermediate Similarity	NPC128496
0.8235	Intermediate Similarity	NPC269267
0.8228	Intermediate Similarity	NPC63020
0.8219	Intermediate Similarity	NPC103734
0.8214	Intermediate Similarity	NPC136948
0.8214	Intermediate Similarity	NPC236618
0.8214	Intermediate Similarity	NPC128644
0.8193	Intermediate Similarity	NPC294438
0.8193	Intermediate Similarity	NPC201655
0.8193	Intermediate Similarity	NPC264317
0.8193	Intermediate Similarity	NPC29447
0.8171	Intermediate Similarity	NPC167103
0.8171	Intermediate Similarity	NPC83569
0.8171	Intermediate Similarity	NPC69279
0.8171	Intermediate Similarity	NPC477852
0.8171	Intermediate Similarity	NPC471037
0.8158	Intermediate Similarity	NPC72343
0.8133	Intermediate Similarity	NPC474962
0.8125	Intermediate Similarity	NPC201459
0.8125	Intermediate Similarity	NPC231431
0.8118	Intermediate Similarity	NPC48824
0.8118	Intermediate Similarity	NPC255176
0.8118	Intermediate Similarity	NPC254572
0.8118	Intermediate Similarity	NPC4309
0.8118	Intermediate Similarity	NPC229407
0.8118	Intermediate Similarity	NPC250687
0.8108	Intermediate Similarity	NPC474221
0.8108	Intermediate Similarity	NPC130459
0.8108	Intermediate Similarity	NPC478180
0.8095	Intermediate Similarity	NPC80590
0.8095	Intermediate Similarity	NPC472869
0.8095	Intermediate Similarity	NPC12774
0.8095	Intermediate Similarity	NPC2783
0.8095	Intermediate Similarity	NPC155011
0.8077	Intermediate Similarity	NPC39362
0.8072	Intermediate Similarity	NPC165064
0.8072	Intermediate Similarity	NPC263974
0.8049	Intermediate Similarity	NPC170985
0.8049	Intermediate Similarity	NPC145143
0.8046	Intermediate Similarity	NPC470113
0.8026	Intermediate Similarity	NPC235586
0.8025	Intermediate Similarity	NPC37038
0.8025	Intermediate Similarity	NPC164999
0.8023	Intermediate Similarity	NPC262043
0.8023	Intermediate Similarity	NPC474570
0.8023	Intermediate Similarity	NPC66344
0.8	Intermediate Similarity	NPC142361
0.8	Intermediate Similarity	NPC33768
0.8	Intermediate Similarity	NPC179028
0.8	Intermediate Similarity	NPC134197
0.8	Intermediate Similarity	NPC96496
0.8	Intermediate Similarity	NPC264005
0.8	Intermediate Similarity	NPC474684
0.8	Intermediate Similarity	NPC269360
0.8	Intermediate Similarity	NPC321514
0.7976	Intermediate Similarity	NPC76518
0.7975	Intermediate Similarity	NPC476601
0.7975	Intermediate Similarity	NPC104806
0.7975	Intermediate Similarity	NPC89294
0.7973	Intermediate Similarity	NPC42060
0.7952	Intermediate Similarity	NPC310470
0.7952	Intermediate Similarity	NPC168188
0.7952	Intermediate Similarity	NPC470015
0.7949	Intermediate Similarity	NPC255168
0.7931	Intermediate Similarity	NPC471896
0.7927	Intermediate Similarity	NPC327002
0.7927	Intermediate Similarity	NPC142244
0.7927	Intermediate Similarity	NPC103754
0.7927	Intermediate Similarity	NPC474484
0.7922	Intermediate Similarity	NPC160817
0.7907	Intermediate Similarity	NPC471900
0.7907	Intermediate Similarity	NPC472870
0.7907	Intermediate Similarity	NPC16377
0.7907	Intermediate Similarity	NPC211162
0.7907	Intermediate Similarity	NPC474719
0.7907	Intermediate Similarity	NPC183374
0.7901	Intermediate Similarity	NPC263951
0.7901	Intermediate Similarity	NPC471475
0.7901	Intermediate Similarity	NPC196827
0.7901	Intermediate Similarity	NPC274996
0.7895	Intermediate Similarity	NPC196197
0.7889	Intermediate Similarity	NPC327788
0.7882	Intermediate Similarity	NPC472505
0.7882	Intermediate Similarity	NPC28252
0.7882	Intermediate Similarity	NPC55309
0.7875	Intermediate Similarity	NPC471899
0.7875	Intermediate Similarity	NPC107039
0.7875	Intermediate Similarity	NPC106078
0.7875	Intermediate Similarity	NPC74685
0.7875	Intermediate Similarity	NPC471897
0.7865	Intermediate Similarity	NPC124207
0.7857	Intermediate Similarity	NPC475509
0.7857	Intermediate Similarity	NPC472864
0.7857	Intermediate Similarity	NPC19849
0.7857	Intermediate Similarity	NPC164577
0.7848	Intermediate Similarity	NPC279666
0.7848	Intermediate Similarity	NPC192540
0.7848	Intermediate Similarity	NPC476844
0.7841	Intermediate Similarity	NPC471901
0.7841	Intermediate Similarity	NPC160506
0.7841	Intermediate Similarity	NPC476187
0.7841	Intermediate Similarity	NPC475416
0.7841	Intermediate Similarity	NPC471747
0.7831	Intermediate Similarity	NPC474605
0.7831	Intermediate Similarity	NPC240302
0.7831	Intermediate Similarity	NPC193347
0.7831	Intermediate Similarity	NPC476292
0.7831	Intermediate Similarity	NPC296367
0.7821	Intermediate Similarity	NPC177826
0.7821	Intermediate Similarity	NPC472813
0.7816	Intermediate Similarity	NPC57954
0.7816	Intermediate Similarity	NPC24772
0.7816	Intermediate Similarity	NPC474704
0.7816	Intermediate Similarity	NPC474889
0.7816	Intermediate Similarity	NPC213832
0.7816	Intermediate Similarity	NPC476733
0.7816	Intermediate Similarity	NPC220498
0.7816	Intermediate Similarity	NPC475921
0.7816	Intermediate Similarity	NPC247312
0.7816	Intermediate Similarity	NPC116146
0.7816	Intermediate Similarity	NPC271974
0.7816	Intermediate Similarity	NPC215029
0.7805	Intermediate Similarity	NPC206735
0.7792	Intermediate Similarity	NPC108131
0.7792	Intermediate Similarity	NPC477850
0.7792	Intermediate Similarity	NPC163020
0.7791	Intermediate Similarity	NPC159046
0.7791	Intermediate Similarity	NPC167877
0.7791	Intermediate Similarity	NPC187376
0.7791	Intermediate Similarity	NPC233836
0.7778	Intermediate Similarity	NPC84383
0.7778	Intermediate Similarity	NPC266431
0.7778	Intermediate Similarity	NPC293052
0.7778	Intermediate Similarity	NPC280654
0.7778	Intermediate Similarity	NPC110094
0.7778	Intermediate Similarity	NPC263135
0.7778	Intermediate Similarity	NPC260385
0.7778	Intermediate Similarity	NPC288906
0.7778	Intermediate Similarity	NPC476174
0.7778	Intermediate Similarity	NPC279974
0.7765	Intermediate Similarity	NPC94531
0.7765	Intermediate Similarity	NPC98270
0.7765	Intermediate Similarity	NPC311702
0.7765	Intermediate Similarity	NPC123319
0.7753	Intermediate Similarity	NPC473690
0.7753	Intermediate Similarity	NPC477855
0.7753	Intermediate Similarity	NPC471902
0.7753	Intermediate Similarity	NPC287118
0.775	Intermediate Similarity	NPC69143
0.7738	Intermediate Similarity	NPC472743
0.7738	Intermediate Similarity	NPC175410
0.7738	Intermediate Similarity	NPC97913
0.7738	Intermediate Similarity	NPC475726
0.7733	Intermediate Similarity	NPC39462
0.7733	Intermediate Similarity	NPC96812
0.7733	Intermediate Similarity	NPC189917

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 NPC321690 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	2207
0.2-0.3	4394
0.3-0.4	1536
0.4-0.5	452
0.5-0.6	161
0.6-0.7	183
0.7-0.8	61
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
0.8193	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD4788	Approved
0.7841	Intermediate Similarity	NPD8034	Phase 2
0.7841	Intermediate Similarity	NPD8035	Phase 2
0.7831	Intermediate Similarity	NPD4221	Approved
0.7831	Intermediate Similarity	NPD4223	Phase 3
0.7765	Intermediate Similarity	NPD5329	Approved
0.7733	Intermediate Similarity	NPD4224	Phase 2
0.7692	Intermediate Similarity	NPD6081	Approved
0.7674	Intermediate Similarity	NPD6098	Approved
0.7647	Intermediate Similarity	NPD4197	Approved
0.7647	Intermediate Similarity	NPD4786	Approved
0.7556	Intermediate Similarity	NPD6399	Phase 3
0.7532	Intermediate Similarity	NPD5360	Phase 3
0.7532	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4689	Approved
0.7471	Intermediate Similarity	NPD4693	Phase 3
0.7471	Intermediate Similarity	NPD4138	Approved
0.7471	Intermediate Similarity	NPD4690	Approved
0.7471	Intermediate Similarity	NPD5205	Approved
0.7471	Intermediate Similarity	NPD4688	Approved
0.7444	Intermediate Similarity	NPD5284	Approved
0.7444	Intermediate Similarity	NPD5281	Approved
0.7419	Intermediate Similarity	NPD6083	Phase 2
0.7419	Intermediate Similarity	NPD6084	Phase 2
0.7416	Intermediate Similarity	NPD6673	Approved
0.7416	Intermediate Similarity	NPD6904	Approved
0.7416	Intermediate Similarity	NPD6080	Approved
0.7412	Intermediate Similarity	NPD3667	Approved
0.7407	Intermediate Similarity	NPD3702	Approved
0.7391	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3617	Approved
0.7317	Intermediate Similarity	NPD6117	Approved
0.7303	Intermediate Similarity	NPD5737	Approved
0.7303	Intermediate Similarity	NPD6672	Approved
0.7303	Intermediate Similarity	NPD5208	Approved
0.7294	Intermediate Similarity	NPD4139	Approved
0.7294	Intermediate Similarity	NPD4692	Approved
0.7283	Intermediate Similarity	NPD6001	Approved
0.7273	Intermediate Similarity	NPD7146	Approved
0.7273	Intermediate Similarity	NPD5280	Approved
0.7273	Intermediate Similarity	NPD6684	Approved
0.7273	Intermediate Similarity	NPD5330	Approved
0.7273	Intermediate Similarity	NPD7334	Approved
0.7273	Intermediate Similarity	NPD4694	Approved
0.7273	Intermediate Similarity	NPD7521	Approved
0.7273	Intermediate Similarity	NPD5690	Phase 2
0.7273	Intermediate Similarity	NPD6409	Approved
0.725	Intermediate Similarity	NPD4243	Approved
0.7241	Intermediate Similarity	NPD3666	Approved
0.7241	Intermediate Similarity	NPD3665	Phase 1
0.7241	Intermediate Similarity	NPD3133	Approved
0.7229	Intermediate Similarity	NPD6116	Phase 1
0.7222	Intermediate Similarity	NPD4753	Phase 2
0.7222	Intermediate Similarity	NPD5328	Approved
0.7204	Intermediate Similarity	NPD5695	Phase 3
0.7158	Intermediate Similarity	NPD5696	Approved
0.7143	Intermediate Similarity	NPD6114	Approved
0.7143	Intermediate Similarity	NPD6115	Approved
0.7143	Intermediate Similarity	NPD6118	Approved
0.7143	Intermediate Similarity	NPD6697	Approved
0.7125	Intermediate Similarity	NPD4789	Approved
0.7111	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6903	Approved
0.7079	Intermediate Similarity	NPD3618	Phase 1
0.7079	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4785	Approved
0.7073	Intermediate Similarity	NPD4784	Approved
0.7065	Intermediate Similarity	NPD6079	Approved
0.7065	Intermediate Similarity	NPD6050	Approved
0.7065	Intermediate Similarity	NPD5693	Phase 1
0.7059	Intermediate Similarity	NPD4195	Approved
0.7037	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4758	Discontinued
0.7037	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4202	Approved
0.6989	Remote Similarity	NPD5133	Approved
0.6957	Remote Similarity	NPD5207	Approved
0.6957	Remote Similarity	NPD5692	Phase 3
0.6915	Remote Similarity	NPD7748	Approved
0.6914	Remote Similarity	NPD4244	Approved
0.6914	Remote Similarity	NPD4747	Approved
0.6914	Remote Similarity	NPD4245	Approved
0.69	Remote Similarity	NPD6675	Approved
0.69	Remote Similarity	NPD5739	Approved
0.69	Remote Similarity	NPD7128	Approved
0.69	Remote Similarity	NPD6402	Approved
0.6889	Remote Similarity	NPD5279	Phase 3
0.6889	Remote Similarity	NPD4519	Discontinued
0.6889	Remote Similarity	NPD4623	Approved
0.6882	Remote Similarity	NPD7515	Phase 2
0.6882	Remote Similarity	NPD5694	Approved
0.6867	Remote Similarity	NPD6924	Approved
0.6867	Remote Similarity	NPD6926	Approved
0.6854	Remote Similarity	NPD3668	Phase 3
0.6848	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4629	Approved
0.6842	Remote Similarity	NPD5210	Approved
0.6829	Remote Similarity	NPD5777	Approved
0.679	Remote Similarity	NPD3698	Phase 2
0.679	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.679	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4137	Phase 3
0.6786	Remote Similarity	NPD5275	Approved
0.6786	Remote Similarity	NPD4190	Phase 3
0.6786	Remote Similarity	NPD6942	Approved
0.6786	Remote Similarity	NPD7339	Approved
0.6782	Remote Similarity	NPD7525	Registered
0.6782	Remote Similarity	NPD4695	Discontinued
0.6774	Remote Similarity	NPD4096	Approved
0.6765	Remote Similarity	NPD7320	Approved
0.6765	Remote Similarity	NPD6899	Approved
0.6765	Remote Similarity	NPD6881	Approved
0.6744	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5364	Discontinued
0.6735	Remote Similarity	NPD6404	Discontinued
0.6731	Remote Similarity	NPD8130	Phase 1
0.6707	Remote Similarity	NPD4691	Approved
0.6706	Remote Similarity	NPD6933	Approved
0.6701	Remote Similarity	NPD5959	Approved
0.6701	Remote Similarity	NPD4755	Approved
0.6701	Remote Similarity	NPD7902	Approved
0.6699	Remote Similarity	NPD6372	Approved
0.6699	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD5733	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6883	Approved
0.6635	Remote Similarity	NPD7102	Approved
0.6635	Remote Similarity	NPD7290	Approved
0.6633	Remote Similarity	NPD7638	Approved
0.663	Remote Similarity	NPD3573	Approved
0.6629	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6011	Approved
0.6598	Remote Similarity	NPD5221	Approved
0.6598	Remote Similarity	NPD4697	Phase 3
0.6598	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5222	Approved
0.6571	Remote Similarity	NPD6650	Approved
0.6571	Remote Similarity	NPD6847	Approved
0.6571	Remote Similarity	NPD6649	Approved
0.6571	Remote Similarity	NPD6869	Approved
0.6571	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6617	Approved
0.6566	Remote Similarity	NPD5286	Approved
0.6566	Remote Similarity	NPD4696	Approved
0.6566	Remote Similarity	NPD7639	Approved
0.6566	Remote Similarity	NPD5285	Approved
0.6566	Remote Similarity	NPD4700	Approved
0.6566	Remote Similarity	NPD7640	Approved
0.6559	Remote Similarity	NPD4518	Approved
0.6538	Remote Similarity	NPD6012	Approved
0.6538	Remote Similarity	NPD6014	Approved
0.6538	Remote Similarity	NPD6013	Approved
0.6535	Remote Similarity	NPD6052	Approved
0.6531	Remote Similarity	NPD5173	Approved
0.6512	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6882	Approved
0.65	Remote Similarity	NPD5223	Approved
0.6495	Remote Similarity	NPD5654	Approved
0.6489	Remote Similarity	NPD6051	Approved
0.6471	Remote Similarity	NPD4687	Approved
0.6471	Remote Similarity	NPD4058	Approved
0.6449	Remote Similarity	NPD8133	Approved
0.6436	Remote Similarity	NPD5091	Approved
0.6436	Remote Similarity	NPD5226	Approved
0.6436	Remote Similarity	NPD5211	Phase 2
0.6436	Remote Similarity	NPD4633	Approved
0.6436	Remote Similarity	NPD5225	Approved
0.6436	Remote Similarity	NPD5224	Approved
0.6429	Remote Similarity	NPD5276	Approved
0.6429	Remote Similarity	NPD7614	Phase 1
0.6422	Remote Similarity	NPD7115	Discovery
0.6408	Remote Similarity	NPD6008	Approved
0.6404	Remote Similarity	NPD6931	Approved
0.6404	Remote Similarity	NPD6930	Phase 2
0.6395	Remote Similarity	NPD3703	Phase 2
0.6392	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7900	Approved
0.6386	Remote Similarity	NPD6923	Approved
0.6386	Remote Similarity	NPD6922	Approved
0.6374	Remote Similarity	NPD5362	Discontinued
0.6373	Remote Similarity	NPD5175	Approved
0.6373	Remote Similarity	NPD4754	Approved
0.6373	Remote Similarity	NPD5174	Approved
0.6354	Remote Similarity	NPD7637	Suspended
0.6346	Remote Similarity	NPD6614	Approved
0.6333	Remote Similarity	NPD5369	Approved
0.6311	Remote Similarity	NPD5141	Approved
0.631	Remote Similarity	NPD7143	Approved
0.631	Remote Similarity	NPD7144	Approved
0.6296	Remote Similarity	NPD4632	Approved
0.6296	Remote Similarity	NPD7341	Phase 2
0.6292	Remote Similarity	NPD6929	Approved
0.6282	Remote Similarity	NPD3198	Approved
0.6267	Remote Similarity	NPD615	Clinical (unspecified phase)

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