NPASS Compound

Structure

NPC21776 OpenBabel07101718312D 26 30 0 0 1 0 0 0 0 0999 V2000 1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5217 -2.3317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7137 -0.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7192 -0.2955 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 -6.5327 -2.1226 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 -3.9559 -2.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1205 -1.3136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1314 -1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 1 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 -5.5382 -2.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 1 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1150 -1.4181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9504 -2.8271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 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 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 21 1 0 0 0 0 8 11 2 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 24 1 0 0 0 0 11 23 1 0 0 0 0 12 17 2 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 10 1 6 0 0 0 15 18 1 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 18 12 1 6 0 0 0 18 25 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.13
Volume:	354.486
LogP:	5.115
LogD:	4.2
LogS:	-4.183
# Rotatable Bonds:	1
TPSA:	57.15
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.834
Synthetic Accessibility Score:	3.806
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.843
MDCK Permeability:	1.443491692043608e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	100.18061065673828%
Volume Distribution (VD):	0.664
Pgp-substrate:	2.3764562606811523%

ADMET: Metabolism

CYP1A2-inhibitor:	0.708
CYP1A2-substrate:	0.882
CYP2C19-inhibitor:	0.856
CYP2C19-substrate:	0.764
CYP2C9-inhibitor:	0.907
CYP2C9-substrate:	0.927
CYP2D6-inhibitor:	0.91
CYP2D6-substrate:	0.842
CYP3A4-inhibitor:	0.787
CYP3A4-substrate:	0.701

ADMET: Excretion

Clearance (CL):	1.849
Half-life (T1/2):	0.159

ADMET: Toxicity

hERG Blockers:	0.412
Human Hepatotoxicity (H-HT):	0.935
Drug-inuced Liver Injury (DILI):	0.699
AMES Toxicity:	0.486
Rat Oral Acute Toxicity:	0.819
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.875
Carcinogencity:	0.52
Eye Corrosion:	0.003
Eye Irritation:	0.2
Respiratory Toxicity:	0.815

Download Data

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

Natural Product: NPC21776

Natural Product ID:	NPC21776
*Common Name:**	Lespeflorin G12
IUPAC Name:	n.a.
Synonyms:	Lespeflorin G12
Standard InCHIKey:	VWRAKYMXGMVCQG-YJBOKZPZSA-N
Standard InCHI:	InChI=1S/C21H20O5/c1-21(2)7-6-13-19-14(9-16(22)20(13)26-21)15-10-24-17-8-11(23-3)4-5-12(17)18(15)25-19/h4-9,15,18,22H,10H2,1-3H3/t15-,18-/m0/s1
SMILES:	COc1ccc2c(c1)OC[C@@H]1[C@H]2Oc2c1cc(c1c2C=CC(O1)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL562225
PubChem CID:	25243328
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	Species	Fabaceae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	8340.0	nM	PMID[526622]

☑ 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 NPC21776 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	465
0.1-0.2	1569
0.2-0.3	4179
0.3-0.4	11373
0.4-0.5	7085
0.5-0.6	3906
0.6-0.7	6536
0.7-0.8	5715
0.8-0.85	1024
0.85-0.9	637
0.9-0.95	175
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC16269
0.9784	High Similarity	NPC45257
0.9784	High Similarity	NPC12641
0.9784	High Similarity	NPC93323
0.9784	High Similarity	NPC280092
0.9716	High Similarity	NPC101376
0.9712	High Similarity	NPC85264
0.9712	High Similarity	NPC47633
0.9712	High Similarity	NPC102044
0.9653	High Similarity	NPC160196
0.9643	High Similarity	NPC63879
0.964	High Similarity	NPC2613
0.964	High Similarity	NPC107161
0.964	High Similarity	NPC204347
0.964	High Similarity	NPC475891
0.964	High Similarity	NPC59841
0.9574	High Similarity	NPC469557
0.9568	High Similarity	NPC247291
0.9521	High Similarity	NPC80918
0.9521	High Similarity	NPC188578
0.9521	High Similarity	NPC159922
0.9496	High Similarity	NPC27495
0.9496	High Similarity	NPC309124
0.9496	High Similarity	NPC254759
0.9496	High Similarity	NPC259519
0.9496	High Similarity	NPC160283
0.9496	High Similarity	NPC184797
0.9429	High Similarity	NPC87725
0.9429	High Similarity	NPC263261
0.9429	High Similarity	NPC471389
0.9424	High Similarity	NPC25966
0.9424	High Similarity	NPC70682
0.9424	High Similarity	NPC292882
0.9424	High Similarity	NPC127218
0.9424	High Similarity	NPC232164
0.9424	High Similarity	NPC260741
0.9424	High Similarity	NPC236306
0.9424	High Similarity	NPC319647
0.9424	High Similarity	NPC245207
0.9424	High Similarity	NPC473739
0.9371	High Similarity	NPC233980
0.9366	High Similarity	NPC473108
0.9366	High Similarity	NPC50250
0.9353	High Similarity	NPC107551
0.9353	High Similarity	NPC474282
0.9353	High Similarity	NPC102904
0.9353	High Similarity	NPC176051
0.9353	High Similarity	NPC326797
0.9353	High Similarity	NPC276490
0.9353	High Similarity	NPC103976
0.9296	High Similarity	NPC477616
0.9291	High Similarity	NPC35216
0.9291	High Similarity	NPC311530
0.9286	High Similarity	NPC471388
0.9281	High Similarity	NPC474639
0.9281	High Similarity	NPC18189
0.9281	High Similarity	NPC227503
0.9281	High Similarity	NPC162659
0.9281	High Similarity	NPC270456
0.9281	High Similarity	NPC173660
0.9281	High Similarity	NPC230734
0.9281	High Similarity	NPC262585
0.9281	High Similarity	NPC20829
0.9281	High Similarity	NPC265433
0.9281	High Similarity	NPC248727
0.9236	High Similarity	NPC260397
0.9214	High Similarity	NPC477938
0.9214	High Similarity	NPC211549
0.9209	High Similarity	NPC112246
0.9209	High Similarity	NPC112939
0.9209	High Similarity	NPC470356
0.9209	High Similarity	NPC151224
0.9209	High Similarity	NPC473413
0.9209	High Similarity	NPC474206
0.9209	High Similarity	NPC94750
0.9209	High Similarity	NPC195022
0.9209	High Similarity	NPC121812
0.9209	High Similarity	NPC134968
0.9184	High Similarity	NPC2745
0.9172	High Similarity	NPC474397
0.9167	High Similarity	NPC307466
0.9161	High Similarity	NPC81638
0.9149	High Similarity	NPC32630
0.9149	High Similarity	NPC475836
0.9143	High Similarity	NPC263367
0.9143	High Similarity	NPC177160
0.9143	High Similarity	NPC16435
0.9143	High Similarity	NPC156502
0.9143	High Similarity	NPC477939
0.9143	High Similarity	NPC29799
0.9143	High Similarity	NPC470802
0.9143	High Similarity	NPC209985
0.9143	High Similarity	NPC269091
0.9143	High Similarity	NPC472334
0.9143	High Similarity	NPC302701
0.9143	High Similarity	NPC306441
0.9143	High Similarity	NPC10737
0.9143	High Similarity	NPC472336
0.9143	High Similarity	NPC54743
0.9137	High Similarity	NPC49603
0.9137	High Similarity	NPC225696
0.9137	High Similarity	NPC187616
0.9137	High Similarity	NPC296915
0.9137	High Similarity	NPC223008
0.9137	High Similarity	NPC117048
0.9137	High Similarity	NPC106215
0.9137	High Similarity	NPC198154
0.9137	High Similarity	NPC97834
0.9137	High Similarity	NPC124085
0.9137	High Similarity	NPC193026
0.9137	High Similarity	NPC115335
0.9137	High Similarity	NPC474478
0.9137	High Similarity	NPC317380
0.9122	High Similarity	NPC157783
0.9116	High Similarity	NPC158784
0.9116	High Similarity	NPC195561
0.911	High Similarity	NPC166584
0.911	High Similarity	NPC20757
0.911	High Similarity	NPC71726
0.911	High Similarity	NPC301961
0.911	High Similarity	NPC227516
0.911	High Similarity	NPC473876
0.9078	High Similarity	NPC474687
0.9071	High Similarity	NPC472337
0.9071	High Similarity	NPC234333
0.9071	High Similarity	NPC47398
0.9071	High Similarity	NPC164787
0.9071	High Similarity	NPC61946
0.9071	High Similarity	NPC260898
0.9065	High Similarity	NPC85435
0.9065	High Similarity	NPC168059
0.9065	High Similarity	NPC92805
0.9065	High Similarity	NPC158331
0.9065	High Similarity	NPC229442
0.9065	High Similarity	NPC11060
0.9054	High Similarity	NPC302915
0.9048	High Similarity	NPC211561
0.9034	High Similarity	NPC90645
0.9034	High Similarity	NPC221318
0.9034	High Similarity	NPC181615
0.9034	High Similarity	NPC472457
0.9028	High Similarity	NPC258083
0.9028	High Similarity	NPC474104
0.9021	High Similarity	NPC178054
0.9021	High Similarity	NPC265075
0.9014	High Similarity	NPC19869
0.9007	High Similarity	NPC3049
0.9007	High Similarity	NPC78047
0.9007	High Similarity	NPC234952
0.9	High Similarity	NPC287745
0.9	High Similarity	NPC16485
0.9	High Similarity	NPC478085
0.8993	High Similarity	NPC175067
0.8993	High Similarity	NPC204215
0.8993	High Similarity	NPC86655
0.8993	High Similarity	NPC13005
0.8993	High Similarity	NPC325860
0.8993	High Similarity	NPC202762
0.8993	High Similarity	NPC6451
0.8993	High Similarity	NPC127624
0.8986	High Similarity	NPC472710
0.8986	High Similarity	NPC477612
0.8986	High Similarity	NPC472709
0.898	High Similarity	NPC212142
0.898	High Similarity	NPC473408
0.8973	High Similarity	NPC226540
0.8973	High Similarity	NPC211758
0.8973	High Similarity	NPC162193
0.8973	High Similarity	NPC87794
0.8973	High Similarity	NPC317053
0.8973	High Similarity	NPC324492
0.8966	High Similarity	NPC469795
0.8958	High Similarity	NPC41782
0.8951	High Similarity	NPC22317
0.8936	High Similarity	NPC126409
0.8936	High Similarity	NPC256262
0.8936	High Similarity	NPC99572
0.8929	High Similarity	NPC263064
0.8929	High Similarity	NPC26394
0.8929	High Similarity	NPC475840
0.8921	High Similarity	NPC211413
0.8921	High Similarity	NPC162801
0.8921	High Similarity	NPC232275
0.8921	High Similarity	NPC268917
0.8921	High Similarity	NPC129784
0.8921	High Similarity	NPC474356
0.8921	High Similarity	NPC228369
0.8921	High Similarity	NPC206224
0.8921	High Similarity	NPC12275
0.8921	High Similarity	NPC476166
0.8921	High Similarity	NPC207892
0.8921	High Similarity	NPC164574
0.8921	High Similarity	NPC118114
0.8921	High Similarity	NPC293203
0.8921	High Similarity	NPC17343
0.8921	High Similarity	NPC129106
0.8921	High Similarity	NPC68205
0.8921	High Similarity	NPC118683
0.8921	High Similarity	NPC300875
0.8921	High Similarity	NPC12875

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 NPC21776 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	894
0.2-0.3	1879
0.3-0.4	2743
0.4-0.5	1585
0.5-0.6	894
0.6-0.7	612
0.7-0.8	154
0.8-0.85	7
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8857	High Similarity	NPD1612	Clinical (unspecified phase)
0.8857	High Similarity	NPD1613	Approved
0.8705	High Similarity	NPD1529	Clinical (unspecified phase)
0.8643	High Similarity	NPD3027	Phase 3
0.8633	High Similarity	NPD1530	Clinical (unspecified phase)
0.8582	High Similarity	NPD4907	Clinical (unspecified phase)
0.844	Intermediate Similarity	NPD4908	Phase 1
0.8369	Intermediate Similarity	NPD2861	Phase 2
0.8201	Intermediate Similarity	NPD1610	Phase 2
0.8153	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD4625	Phase 3
0.8125	Intermediate Similarity	NPD5494	Approved
0.8089	Intermediate Similarity	NPD1934	Approved
0.8065	Intermediate Similarity	NPD1653	Approved
0.8038	Intermediate Similarity	NPD2801	Approved
0.7958	Intermediate Similarity	NPD4749	Approved
0.795	Intermediate Similarity	NPD6234	Discontinued
0.7945	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1548	Phase 1
0.7895	Intermediate Similarity	NPD6674	Discontinued
0.7892	Intermediate Similarity	NPD5844	Phase 1
0.7831	Intermediate Similarity	NPD7228	Approved
0.7826	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6166	Phase 2
0.7785	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD5124	Phase 1
0.7778	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD37	Approved
0.7725	Intermediate Similarity	NPD3818	Discontinued
0.7718	Intermediate Similarity	NPD4060	Phase 1
0.7716	Intermediate Similarity	NPD4965	Approved
0.7716	Intermediate Similarity	NPD4966	Approved
0.7716	Intermediate Similarity	NPD3882	Suspended
0.7716	Intermediate Similarity	NPD4967	Phase 2
0.7706	Intermediate Similarity	NPD7549	Discontinued
0.7679	Intermediate Similarity	NPD7054	Approved
0.7636	Intermediate Similarity	NPD7199	Phase 2
0.7633	Intermediate Similarity	NPD7074	Phase 3
0.7633	Intermediate Similarity	NPD7472	Approved
0.7625	Intermediate Similarity	NPD4380	Phase 2
0.7619	Intermediate Similarity	NPD3018	Phase 2
0.7602	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3620	Phase 2
0.76	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1511	Approved
0.7571	Intermediate Similarity	NPD6671	Approved
0.7554	Intermediate Similarity	NPD5283	Phase 1
0.7545	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6696	Suspended
0.7529	Intermediate Similarity	NPD4663	Approved
0.7516	Intermediate Similarity	NPD5588	Approved
0.7516	Intermediate Similarity	NPD5058	Phase 3
0.75	Intermediate Similarity	NPD6331	Phase 2
0.7486	Intermediate Similarity	NPD7906	Approved
0.7485	Intermediate Similarity	NPD6797	Phase 2
0.7484	Intermediate Similarity	NPD1512	Approved
0.7471	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7213	Phase 3
0.7468	Intermediate Similarity	NPD7212	Phase 2
0.7466	Intermediate Similarity	NPD2983	Phase 2
0.7466	Intermediate Similarity	NPD2982	Phase 2
0.7457	Intermediate Similarity	NPD7310	Approved
0.7457	Intermediate Similarity	NPD7311	Approved
0.7457	Intermediate Similarity	NPD7312	Approved
0.7457	Intermediate Similarity	NPD7313	Approved
0.7457	Intermediate Similarity	NPD4578	Approved
0.7457	Intermediate Similarity	NPD4577	Approved
0.7451	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4538	Approved
0.7451	Intermediate Similarity	NPD4536	Approved
0.7442	Intermediate Similarity	NPD7251	Discontinued
0.7439	Intermediate Similarity	NPD3817	Phase 2
0.7439	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7447	Phase 1
0.7421	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD8651	Approved
0.7414	Intermediate Similarity	NPD7309	Approved
0.741	Intermediate Similarity	NPD228	Approved
0.7399	Intermediate Similarity	NPD7808	Phase 3
0.7397	Intermediate Similarity	NPD2981	Phase 2
0.7396	Intermediate Similarity	NPD2489	Approved
0.7396	Intermediate Similarity	NPD27	Approved
0.7389	Intermediate Similarity	NPD7466	Approved
0.7378	Intermediate Similarity	NPD1465	Phase 2
0.7355	Intermediate Similarity	NPD6100	Approved
0.7355	Intermediate Similarity	NPD6099	Approved
0.7349	Intermediate Similarity	NPD7075	Discontinued
0.7349	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7240	Approved
0.7341	Intermediate Similarity	NPD6559	Discontinued
0.7337	Intermediate Similarity	NPD2969	Approved
0.7337	Intermediate Similarity	NPD2970	Approved
0.7329	Intermediate Similarity	NPD3705	Approved
0.7329	Intermediate Similarity	NPD1091	Approved
0.7325	Intermediate Similarity	NPD1652	Phase 2
0.7315	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7266	Discontinued
0.7308	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5960	Phase 3
0.729	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3051	Approved
0.7278	Intermediate Similarity	NPD6232	Discontinued
0.7273	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5929	Approved
0.7267	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3021	Approved
0.7266	Intermediate Similarity	NPD3022	Approved
0.7261	Intermediate Similarity	NPD2424	Discontinued
0.7256	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1558	Phase 1
0.7251	Intermediate Similarity	NPD7473	Discontinued
0.7246	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5402	Approved
0.7229	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1247	Approved
0.7219	Intermediate Similarity	NPD6959	Discontinued
0.7216	Intermediate Similarity	NPD8053	Approved
0.7216	Intermediate Similarity	NPD8054	Approved
0.7215	Intermediate Similarity	NPD5177	Phase 3
0.7211	Intermediate Similarity	NPD422	Phase 1
0.7208	Intermediate Similarity	NPD6355	Discontinued
0.7208	Intermediate Similarity	NPD5735	Approved
0.7205	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5762	Approved
0.7197	Intermediate Similarity	NPD5763	Approved
0.7195	Intermediate Similarity	NPD4675	Approved
0.7195	Intermediate Similarity	NPD4678	Approved
0.7176	Intermediate Similarity	NPD3787	Discontinued
0.7176	Intermediate Similarity	NPD7229	Phase 3
0.717	Intermediate Similarity	NPD3750	Approved
0.717	Intermediate Similarity	NPD3892	Phase 2
0.7169	Intermediate Similarity	NPD7819	Suspended
0.7153	Intermediate Similarity	NPD7340	Approved
0.7152	Intermediate Similarity	NPD1549	Phase 2
0.7134	Intermediate Similarity	NPD4005	Discontinued
0.7115	Intermediate Similarity	NPD7097	Phase 1
0.7108	Intermediate Similarity	NPD6801	Discontinued
0.7089	Intermediate Similarity	NPD1375	Discontinued
0.7089	Intermediate Similarity	NPD3540	Phase 1
0.7083	Intermediate Similarity	NPD7157	Approved
0.7083	Intermediate Similarity	NPD7768	Phase 2
0.7078	Intermediate Similarity	NPD6233	Phase 2
0.7071	Intermediate Similarity	NPD2684	Approved
0.707	Intermediate Similarity	NPD7033	Discontinued
0.7066	Intermediate Similarity	NPD8455	Phase 2
0.7063	Intermediate Similarity	NPD4110	Phase 3
0.7063	Intermediate Similarity	NPD1398	Phase 1
0.7063	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7095	Approved
0.7055	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD968	Approved
0.7048	Intermediate Similarity	NPD6072	Discontinued
0.7048	Intermediate Similarity	NPD7411	Suspended
0.7045	Intermediate Similarity	NPD7685	Pre-registration
0.7037	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7041	Phase 2
0.7037	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2238	Phase 2
0.7027	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2935	Discontinued
0.7025	Intermediate Similarity	NPD2796	Approved
0.7025	Intermediate Similarity	NPD3539	Phase 1
0.7024	Intermediate Similarity	NPD2560	Approved
0.7024	Intermediate Similarity	NPD2563	Approved
0.7022	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6190	Approved
0.7019	Intermediate Similarity	NPD2677	Approved
0.7018	Intermediate Similarity	NPD8127	Discontinued
0.7013	Intermediate Similarity	NPD6798	Discontinued
0.7011	Intermediate Similarity	NPD3751	Discontinued
0.7007	Intermediate Similarity	NPD1357	Approved
0.7006	Intermediate Similarity	NPD3384	Approved
0.7006	Intermediate Similarity	NPD3382	Approved
0.7006	Intermediate Similarity	NPD3383	Approved
0.7	Intermediate Similarity	NPD5327	Phase 3
0.7	Intermediate Similarity	NPD919	Approved
0.7	Intermediate Similarity	NPD4236	Phase 3
0.7	Intermediate Similarity	NPD4237	Approved
0.7	Intermediate Similarity	NPD290	Approved
0.6994	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7843	Approved
0.6981	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6002	Phase 3
0.6981	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6004	Phase 3

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