NPASS Compound

Structure

NPC213658 OpenBabel07101719252D 28 31 0 0 1 0 0 0 0 0999 V2000 -1.7796 -1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2796 2.9593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7796 2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1691 0.1229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3383 -1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -0.9067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5116 2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1473 -0.0850 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6456 -0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6456 0.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7796 1.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7796 2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 0.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3776 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8904 0.5841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -0.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2518 -1.0796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 1.0933 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 13 1 0 0 0 0 2 14 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 11 15 1 0 0 0 0 11 21 1 0 0 0 0 12 21 1 0 0 0 0 12 26 1 0 0 0 0 13 16 1 0 0 0 0 13 22 1 6 0 0 0 14 23 2 0 0 0 0 14 27 1 0 0 0 0 15 24 1 6 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 1 0 0 0 17 18 1 0 0 0 0 17 27 1 1 0 0 0 18 19 1 0 0 0 0 18 20 1 1 0 0 0 20 22 1 6 0 0 0 21 9 1 6 0 0 0 21 28 1 0 0 0 0 22 10 1 1 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.25
Volume:	404.947
LogP:	2.96
LogD:	2.634
LogS:	-4.221
# Rotatable Bonds:	2
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.663
Synthetic Accessibility Score:	5.765
Fsp3:	0.955
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.975
MDCK Permeability:	4.787739089806564e-05
Pgp-inhibitor:	0.368
Pgp-substrate:	0.968
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.068

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.098
Plasma Protein Binding (PPB):	57.367488861083984%
Volume Distribution (VD):	1.508
Pgp-substrate:	35.79303741455078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.903
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.85
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.641
CYP3A4-substrate:	0.413

ADMET: Excretion

Clearance (CL):	6.892
Half-life (T1/2):	0.347

ADMET: Toxicity

hERG Blockers:	0.193
Human Hepatotoxicity (H-HT):	0.782
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.898
Rat Oral Acute Toxicity:	0.79
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.334
Carcinogencity:	0.464
Eye Corrosion:	0.005
Eye Irritation:	0.015
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC213658

Natural Product ID:	NPC213658
*Common Name:**	XUFKRKJXYWRSRT-RRPHXOACSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XUFKRKJXYWRSRT-RRPHXOACSA-N
Standard InCHI:	InChI=1S/C22H36O6/c1-13-16(25)17(27-14(2)23)18-19(3,4)7-6-8-20(18,5)22(13)10-9-21(28-22)11-15(24)26-12-21/h13,15-18,24-25H,6-12H2,1-5H3/t13-,15-,16-,17-,18+,20+,21+,22-/m1/s1
SMILES:	C[C@@H]1[C@H]([C@H]([C@H]2C(C)(C)CCC[C@]2(C)[C@]21CC[C@@]1(C[C@H](O)OC1)O2)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234599
PubChem CID:	90670462
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO17287	Lagopsis supina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24707938]
NPO17287	Lagopsis supina	Species	Lamiaceae	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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	<	50.0	%	PMID[494322]

☑ 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 NPC213658 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	400
0.1-0.2	3499
0.2-0.3	10334
0.3-0.4	12839
0.4-0.5	6206
0.5-0.6	5564
0.6-0.7	3152
0.7-0.8	631
0.8-0.85	48
0.85-0.9	16
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC110365
1.0	High Similarity	NPC62202
1.0	High Similarity	NPC45833
0.963	High Similarity	NPC18953
0.9195	High Similarity	NPC475307
0.9176	High Similarity	NPC470872
0.9167	High Similarity	NPC471410
0.9167	High Similarity	NPC471411
0.9146	High Similarity	NPC470155
0.9146	High Similarity	NPC477447
0.9146	High Similarity	NPC477446
0.9024	High Similarity	NPC470154
0.9024	High Similarity	NPC470156
0.9024	High Similarity	NPC71541
0.8902	High Similarity	NPC471217
0.8902	High Similarity	NPC471216
0.8824	High Similarity	NPC235402
0.8721	High Similarity	NPC268633
0.8675	High Similarity	NPC472951
0.8675	High Similarity	NPC472943
0.8675	High Similarity	NPC186588
0.8642	High Similarity	NPC107963
0.8588	High Similarity	NPC241959
0.8556	High Similarity	NPC122083
0.8556	High Similarity	NPC256104
0.8556	High Similarity	NPC182740
0.8556	High Similarity	NPC211845
0.8523	High Similarity	NPC476435
0.8506	High Similarity	NPC155531
0.8506	High Similarity	NPC215968
0.8506	High Similarity	NPC474008
0.8506	High Similarity	NPC107603
0.8478	Intermediate Similarity	NPC475785
0.8471	Intermediate Similarity	NPC2096
0.8471	Intermediate Similarity	NPC208912
0.8395	Intermediate Similarity	NPC470151
0.8372	Intermediate Similarity	NPC213737
0.8372	Intermediate Similarity	NPC474284
0.8372	Intermediate Similarity	NPC474253
0.8372	Intermediate Similarity	NPC474346
0.8372	Intermediate Similarity	NPC475820
0.837	Intermediate Similarity	NPC21897
0.8315	Intermediate Similarity	NPC471221
0.8298	Intermediate Similarity	NPC292775
0.8295	Intermediate Similarity	NPC477283
0.828	Intermediate Similarity	NPC203434
0.828	Intermediate Similarity	NPC238796
0.828	Intermediate Similarity	NPC475765
0.828	Intermediate Similarity	NPC237071
0.8256	Intermediate Similarity	NPC60018
0.8256	Intermediate Similarity	NPC154043
0.8256	Intermediate Similarity	NPC202688
0.8214	Intermediate Similarity	NPC43463
0.8214	Intermediate Similarity	NPC177343
0.8214	Intermediate Similarity	NPC272841
0.8211	Intermediate Similarity	NPC51579
0.8202	Intermediate Similarity	NPC5943
0.8193	Intermediate Similarity	NPC136424
0.8182	Intermediate Similarity	NPC266651
0.8172	Intermediate Similarity	NPC57964
0.8172	Intermediate Similarity	NPC94582
0.8161	Intermediate Similarity	NPC111582
0.8161	Intermediate Similarity	NPC477285
0.814	Intermediate Similarity	NPC211049
0.8132	Intermediate Similarity	NPC470114
0.8125	Intermediate Similarity	NPC475574
0.8111	Intermediate Similarity	NPC476379
0.8111	Intermediate Similarity	NPC221993
0.8111	Intermediate Similarity	NPC128475
0.8105	Intermediate Similarity	NPC471375
0.8105	Intermediate Similarity	NPC472144
0.8105	Intermediate Similarity	NPC209798
0.8105	Intermediate Similarity	NPC471374
0.809	Intermediate Similarity	NPC131365
0.8072	Intermediate Similarity	NPC472950
0.8072	Intermediate Similarity	NPC472952
0.8065	Intermediate Similarity	NPC151214
0.8065	Intermediate Similarity	NPC3538
0.8065	Intermediate Similarity	NPC191915
0.8065	Intermediate Similarity	NPC477224
0.8065	Intermediate Similarity	NPC113500
0.8046	Intermediate Similarity	NPC477286
0.8046	Intermediate Similarity	NPC216800
0.8046	Intermediate Similarity	NPC286719
0.8043	Intermediate Similarity	NPC475878
0.8023	Intermediate Similarity	NPC186594
0.8022	Intermediate Similarity	NPC82955
0.8022	Intermediate Similarity	NPC20822
0.8021	Intermediate Similarity	NPC471428
0.8021	Intermediate Similarity	NPC470030
0.8021	Intermediate Similarity	NPC471426
0.8021	Intermediate Similarity	NPC471427
0.8	Intermediate Similarity	NPC472396
0.8	Intermediate Similarity	NPC161928
0.8	Intermediate Similarity	NPC266417
0.8	Intermediate Similarity	NPC191345
0.8	Intermediate Similarity	NPC252483
0.8	Intermediate Similarity	NPC210658
0.8	Intermediate Similarity	NPC472145
0.7978	Intermediate Similarity	NPC290612
0.7957	Intermediate Similarity	NPC311246
0.7957	Intermediate Similarity	NPC167644
0.7952	Intermediate Similarity	NPC308489
0.7938	Intermediate Similarity	NPC108227
0.7938	Intermediate Similarity	NPC472081
0.7938	Intermediate Similarity	NPC476512
0.7935	Intermediate Similarity	NPC18536
0.7935	Intermediate Similarity	NPC50443
0.7931	Intermediate Similarity	NPC190940
0.7931	Intermediate Similarity	NPC116320
0.7931	Intermediate Similarity	NPC119922
0.7907	Intermediate Similarity	NPC477282
0.7907	Intermediate Similarity	NPC81074
0.7895	Intermediate Similarity	NPC156377
0.7895	Intermediate Similarity	NPC296936
0.7895	Intermediate Similarity	NPC252056
0.7882	Intermediate Similarity	NPC476719
0.7865	Intermediate Similarity	NPC79308
0.7865	Intermediate Similarity	NPC65133
0.7865	Intermediate Similarity	NPC320824
0.7857	Intermediate Similarity	NPC114700
0.7857	Intermediate Similarity	NPC470029
0.7857	Intermediate Similarity	NPC134967
0.7857	Intermediate Similarity	NPC310138
0.7849	Intermediate Similarity	NPC210759
0.7849	Intermediate Similarity	NPC293609
0.7849	Intermediate Similarity	NPC149966
0.7849	Intermediate Similarity	NPC5632
0.7849	Intermediate Similarity	NPC229801
0.7849	Intermediate Similarity	NPC473066
0.7849	Intermediate Similarity	NPC307167
0.7841	Intermediate Similarity	NPC477284
0.7816	Intermediate Similarity	NPC475456
0.7816	Intermediate Similarity	NPC474714
0.7812	Intermediate Similarity	NPC477223
0.7812	Intermediate Similarity	NPC477222
0.7802	Intermediate Similarity	NPC43912
0.7802	Intermediate Similarity	NPC140446
0.7789	Intermediate Similarity	NPC477494
0.7778	Intermediate Similarity	NPC478111
0.7778	Intermediate Similarity	NPC476837
0.7778	Intermediate Similarity	NPC97260
0.7778	Intermediate Similarity	NPC139181
0.7766	Intermediate Similarity	NPC224003
0.7766	Intermediate Similarity	NPC35164
0.7766	Intermediate Similarity	NPC323231
0.7766	Intermediate Similarity	NPC171741
0.7766	Intermediate Similarity	NPC18724
0.7766	Intermediate Similarity	NPC470623
0.7766	Intermediate Similarity	NPC277774
0.7755	Intermediate Similarity	NPC477225
0.7753	Intermediate Similarity	NPC470070
0.7753	Intermediate Similarity	NPC69953
0.7745	Intermediate Similarity	NPC305939
0.7742	Intermediate Similarity	NPC473542
0.7742	Intermediate Similarity	NPC279329
0.7738	Intermediate Similarity	NPC166250
0.7738	Intermediate Similarity	NPC472944
0.7738	Intermediate Similarity	NPC472945
0.7732	Intermediate Similarity	NPC473638
0.7717	Intermediate Similarity	NPC56777
0.7717	Intermediate Similarity	NPC201607
0.7708	Intermediate Similarity	NPC145553
0.7708	Intermediate Similarity	NPC116683
0.7701	Intermediate Similarity	NPC477287
0.77	Intermediate Similarity	NPC31430
0.77	Intermediate Similarity	NPC470061
0.77	Intermediate Similarity	NPC470060
0.77	Intermediate Similarity	NPC470057
0.77	Intermediate Similarity	NPC85593
0.77	Intermediate Similarity	NPC470064
0.77	Intermediate Similarity	NPC470043
0.77	Intermediate Similarity	NPC470059
0.77	Intermediate Similarity	NPC470062
0.77	Intermediate Similarity	NPC100078
0.77	Intermediate Similarity	NPC470058
0.7692	Intermediate Similarity	NPC103782
0.7692	Intermediate Similarity	NPC114378
0.7692	Intermediate Similarity	NPC471240
0.7684	Intermediate Similarity	NPC471373
0.7684	Intermediate Similarity	NPC45959
0.7684	Intermediate Similarity	NPC77717
0.7684	Intermediate Similarity	NPC175
0.7684	Intermediate Similarity	NPC148593
0.7684	Intermediate Similarity	NPC30687
0.7684	Intermediate Similarity	NPC473774
0.7684	Intermediate Similarity	NPC267238
0.7684	Intermediate Similarity	NPC252253
0.7684	Intermediate Similarity	NPC24960
0.7684	Intermediate Similarity	NPC305418
0.7684	Intermediate Similarity	NPC253611
0.7674	Intermediate Similarity	NPC474574
0.7674	Intermediate Similarity	NPC133596
0.7674	Intermediate Similarity	NPC64081
0.7674	Intermediate Similarity	NPC11907
0.767	Intermediate Similarity	NPC86217
0.7667	Intermediate Similarity	NPC474156
0.766	Intermediate Similarity	NPC59006
0.766	Intermediate Similarity	NPC219516
0.766	Intermediate Similarity	NPC36372

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 NPC213658 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	417
0.1-0.2	3844
0.2-0.3	3340
0.3-0.4	870
0.4-0.5	375
0.5-0.6	237
0.6-0.7	64
0.7-0.8	3
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
0.759	Intermediate Similarity	NPD7532	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD8171	Discontinued
0.7117	Intermediate Similarity	NPD7516	Approved
0.7073	Intermediate Similarity	NPD371	Approved
0.7033	Intermediate Similarity	NPD6928	Phase 2
0.7027	Intermediate Similarity	NPD7327	Approved
0.7027	Intermediate Similarity	NPD7328	Approved
0.7019	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD3669	Approved
0.6989	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD1811	Approved
0.6932	Remote Similarity	NPD1810	Approved
0.6916	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD1700	Approved
0.686	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6118	Approved
0.6813	Remote Similarity	NPD6114	Approved
0.6813	Remote Similarity	NPD6115	Approved
0.6813	Remote Similarity	NPD6697	Approved
0.6759	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6116	Phase 1
0.6696	Remote Similarity	NPD8380	Approved
0.6696	Remote Similarity	NPD8379	Approved
0.6696	Remote Similarity	NPD8335	Approved
0.6696	Remote Similarity	NPD8378	Approved
0.6696	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD8133	Approved
0.6609	Remote Similarity	NPD8377	Approved
0.6609	Remote Similarity	NPD8294	Approved
0.6593	Remote Similarity	NPD6117	Approved
0.6591	Remote Similarity	NPD2687	Approved
0.6591	Remote Similarity	NPD2686	Approved
0.6591	Remote Similarity	NPD2254	Approved
0.6552	Remote Similarity	NPD8033	Approved
0.6421	Remote Similarity	NPD1779	Approved
0.6421	Remote Similarity	NPD1780	Approved
0.6404	Remote Similarity	NPD6940	Discontinued
0.6396	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6686	Approved
0.6348	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7507	Approved
0.6311	Remote Similarity	NPD7319	Approved
0.6281	Remote Similarity	NPD8293	Discontinued
0.6273	Remote Similarity	NPD6412	Phase 2
0.6271	Remote Similarity	NPD7503	Approved
0.6262	Remote Similarity	NPD5344	Discontinued
0.623	Remote Similarity	NPD7736	Approved
0.622	Remote Similarity	NPD2267	Suspended
0.6218	Remote Similarity	NPD6370	Approved
0.6134	Remote Similarity	NPD6921	Approved
0.6129	Remote Similarity	NPD3703	Phase 2
0.6126	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD7492	Approved
0.6095	Remote Similarity	NPD7991	Discontinued
0.6091	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7638	Approved
0.6075	Remote Similarity	NPD4225	Approved
0.6066	Remote Similarity	NPD6616	Approved
0.605	Remote Similarity	NPD6059	Approved
0.605	Remote Similarity	NPD6054	Approved
0.604	Remote Similarity	NPD7524	Approved
0.6033	Remote Similarity	NPD8328	Phase 3
0.6019	Remote Similarity	NPD7639	Approved
0.6019	Remote Similarity	NPD7640	Approved
0.6016	Remote Similarity	NPD7078	Approved
0.5978	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD8034	Phase 2
0.5962	Remote Similarity	NPD8035	Phase 2
0.5957	Remote Similarity	NPD3702	Approved
0.5934	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7632	Discontinued
0.5902	Remote Similarity	NPD6067	Discontinued
0.5872	Remote Similarity	NPD6648	Approved
0.587	Remote Similarity	NPD4787	Phase 1
0.5868	Remote Similarity	NPD6016	Approved
0.5868	Remote Similarity	NPD6015	Approved
0.5865	Remote Similarity	NPD3168	Discontinued
0.5842	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.582	Remote Similarity	NPD5988	Approved
0.5816	Remote Similarity	NPD7525	Registered
0.5812	Remote Similarity	NPD4632	Approved
0.5806	Remote Similarity	NPD5777	Approved
0.5798	Remote Similarity	NPD6009	Approved
0.5789	Remote Similarity	NPD7320	Approved
0.5785	Remote Similarity	NPD6319	Approved
0.5752	Remote Similarity	NPD5739	Approved
0.5752	Remote Similarity	NPD6402	Approved
0.5752	Remote Similarity	NPD7128	Approved
0.5752	Remote Similarity	NPD6675	Approved
0.5743	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD8297	Approved
0.5726	Remote Similarity	NPD6882	Approved
0.5699	Remote Similarity	NPD4245	Approved
0.5699	Remote Similarity	NPD4244	Approved
0.5667	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD229	Approved
0.5652	Remote Similarity	NPD6899	Approved
0.5652	Remote Similarity	NPD6881	Approved
0.5652	Remote Similarity	NPD5360	Phase 3
0.5652	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD6695	Phase 3
0.5638	Remote Similarity	NPD6081	Approved
0.5625	Remote Similarity	NPD8084	Approved
0.5625	Remote Similarity	NPD8083	Approved
0.5625	Remote Similarity	NPD8138	Approved
0.5625	Remote Similarity	NPD8082	Approved
0.5625	Remote Similarity	NPD8086	Approved
0.5625	Remote Similarity	NPD8085	Approved
0.5625	Remote Similarity	NPD8139	Approved
0.5614	Remote Similarity	NPD6008	Approved
0.561	Remote Similarity	NPD8516	Approved
0.561	Remote Similarity	NPD8517	Approved
0.561	Remote Similarity	NPD8515	Approved
0.561	Remote Similarity	NPD8513	Phase 3
0.5607	Remote Similarity	NPD6399	Phase 3
0.5604	Remote Similarity	NPD4224	Phase 2
0.5603	Remote Similarity	NPD6372	Approved
0.5603	Remote Similarity	NPD6373	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