NPASS Compound

Structure

NPC472820 OpenBabel07101718222D 29 33 0 0 1 0 0 0 0 0999 V2000 8.3123 3.5590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 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 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7142 4.0590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4462 4.0590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 1.3090 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 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9821 3.5590 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8482 3.5590 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4462 5.0590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4821 4.4250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8482 4.5590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 -0.6045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5802 3.5590 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 12 1 0 0 0 0 3 4 1 0 0 0 0 3 13 1 0 0 0 0 4 16 1 0 0 0 0 5 6 1 0 0 0 0 5 14 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 22 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 11 28 1 0 0 0 0 12 23 2 0 0 0 0 12 28 1 0 0 0 0 13 21 1 6 0 0 0 14 15 1 0 0 0 0 14 19 1 1 0 0 0 15 22 1 0 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 17 24 2 0 0 0 0 17 29 1 0 0 0 0 18 20 1 1 0 0 0 18 21 1 0 0 0 0 18 25 1 0 0 0 0 19 2 1 1 0 0 0 20 6 1 1 0 0 0 21 26 1 1 0 0 0 22 27 1 6 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.2
Volume:	399.908
LogP:	1.996
LogD:	1.36
LogS:	-3.65
# Rotatable Bonds:	3
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.595
Synthetic Accessibility Score:	6.268
Fsp3:	0.818
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:	-5.215
MDCK Permeability:	2.248747114208527e-05
Pgp-inhibitor:	0.697
Pgp-substrate:	0.913
Human Intestinal Absorption (HIA):	0.088
20% Bioavailability (F20%):	0.965
30% Bioavailability (F30%):	0.81

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.932
Plasma Protein Binding (PPB):	60.01228713989258%
Volume Distribution (VD):	0.867
Pgp-substrate:	32.916221618652344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.302
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.335
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.066
CYP3A4-inhibitor:	0.649
CYP3A4-substrate:	0.207

ADMET: Excretion

Clearance (CL):	1.872
Half-life (T1/2):	0.702

ADMET: Toxicity

hERG Blockers:	0.308
Human Hepatotoxicity (H-HT):	0.21
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.71
Rat Oral Acute Toxicity:	0.968
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.539
Carcinogencity:	0.323
Eye Corrosion:	0.004
Eye Irritation:	0.032
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC472820

Natural Product ID:	NPC472820
*Common Name:**	NPMVGRUUGRDIQA-BYPZQFJRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NPMVGRUUGRDIQA-BYPZQFJRSA-N
Standard InCHI:	InChI=1S/C22H30O7/c1-12(23)28-11-21(26)13-3-4-16-19(2)7-8-22(27)15(9-17(24)29-22)14(19)5-6-20(16,10-13)18(21)25/h9,13-14,16,18,25-27H,3-8,10-11H2,1-2H3/t13-,14-,16+,18-,19-,20-,21+,22-/m1/s1
SMILES:	CC(=O)OC[C@]1(O)[C@@H]2CC[C@@H]3[C@]([C@H]1O)(C2)CC[C@H]1[C@@]3(C)CC[C@@]2(C1=CC(=O)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3586287
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32576	tricalysia fruticosa	Species	Rubiaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[26052978]

☑ 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	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[469912]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	>	90.0	%	PMID[469912]

☑ 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 NPC472820 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	206
0.1-0.2	1390
0.2-0.3	4587
0.3-0.4	10909
0.4-0.5	10656
0.5-0.6	6175
0.6-0.7	6098
0.7-0.8	2390
0.8-0.85	201
0.85-0.9	67
0.9-0.95	15
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9898	High Similarity	NPC472818
0.9796	High Similarity	NPC472819
0.9388	High Similarity	NPC472826
0.9184	High Similarity	NPC231751
0.9118	High Similarity	NPC186668
0.9109	High Similarity	NPC472821
0.8972	High Similarity	NPC69576
0.8972	High Similarity	NPC471633
0.8972	High Similarity	NPC31354
0.8972	High Similarity	NPC84949
0.8922	High Similarity	NPC97487
0.8922	High Similarity	NPC10232
0.8922	High Similarity	NPC189588
0.8922	High Similarity	NPC187302
0.8922	High Similarity	NPC196471
0.8911	High Similarity	NPC247701
0.8911	High Similarity	NPC295110
0.8911	High Similarity	NPC25177
0.8911	High Similarity	NPC268829
0.8911	High Similarity	NPC222875
0.8889	High Similarity	NPC5311
0.8889	High Similarity	NPC310341
0.8889	High Similarity	NPC99620
0.8889	High Similarity	NPC193382
0.8889	High Similarity	NPC199428
0.8857	High Similarity	NPC475030
0.8835	High Similarity	NPC472822
0.8824	High Similarity	NPC472815
0.8807	High Similarity	NPC473852
0.8807	High Similarity	NPC196429
0.8807	High Similarity	NPC471355
0.8807	High Similarity	NPC152615
0.8807	High Similarity	NPC309034
0.8807	High Similarity	NPC99728
0.8807	High Similarity	NPC50305
0.8807	High Similarity	NPC87250
0.8807	High Similarity	NPC93883
0.8807	High Similarity	NPC84987
0.8807	High Similarity	NPC471351
0.8807	High Similarity	NPC243196
0.8807	High Similarity	NPC34390
0.8807	High Similarity	NPC27507
0.8807	High Similarity	NPC77319
0.8807	High Similarity	NPC474418
0.8807	High Similarity	NPC471354
0.8807	High Similarity	NPC142066
0.8807	High Similarity	NPC244402
0.8807	High Similarity	NPC157376
0.8807	High Similarity	NPC290693
0.8807	High Similarity	NPC158344
0.8807	High Similarity	NPC471353
0.875	High Similarity	NPC220217
0.875	High Similarity	NPC119855
0.8738	High Similarity	NPC160583
0.8727	High Similarity	NPC83287
0.8661	High Similarity	NPC40749
0.8654	High Similarity	NPC200861
0.8649	High Similarity	NPC32177
0.8649	High Similarity	NPC5883
0.8649	High Similarity	NPC236973
0.8649	High Similarity	NPC470897
0.8649	High Similarity	NPC292467
0.8649	High Similarity	NPC329905
0.8649	High Similarity	NPC55532
0.8649	High Similarity	NPC304260
0.8649	High Similarity	NPC469756
0.8649	High Similarity	NPC44899
0.8649	High Similarity	NPC30483
0.8649	High Similarity	NPC29639
0.8636	High Similarity	NPC203862
0.8571	High Similarity	NPC475556
0.8571	High Similarity	NPC72260
0.8571	High Similarity	NPC475136
0.8571	High Similarity	NPC475629
0.8571	High Similarity	NPC474466
0.8496	Intermediate Similarity	NPC173555
0.8496	Intermediate Similarity	NPC231518
0.8496	Intermediate Similarity	NPC475219
0.8496	Intermediate Similarity	NPC475419
0.8496	Intermediate Similarity	NPC475590
0.8496	Intermediate Similarity	NPC314535
0.8496	Intermediate Similarity	NPC474908
0.8496	Intermediate Similarity	NPC120390
0.8491	Intermediate Similarity	NPC471205
0.8447	Intermediate Similarity	NPC38855
0.8421	Intermediate Similarity	NPC264336
0.8421	Intermediate Similarity	NPC115349
0.8421	Intermediate Similarity	NPC74259
0.8421	Intermediate Similarity	NPC474423
0.8421	Intermediate Similarity	NPC193893
0.8411	Intermediate Similarity	NPC472825
0.8411	Intermediate Similarity	NPC38948
0.8393	Intermediate Similarity	NPC218093
0.8381	Intermediate Similarity	NPC281378
0.835	Intermediate Similarity	NPC181147
0.8348	Intermediate Similarity	NPC208193
0.8348	Intermediate Similarity	NPC117445
0.8348	Intermediate Similarity	NPC308262
0.8348	Intermediate Similarity	NPC27363
0.8333	Intermediate Similarity	NPC206618
0.8319	Intermediate Similarity	NPC81222
0.8319	Intermediate Similarity	NPC153085
0.8319	Intermediate Similarity	NPC268326
0.8319	Intermediate Similarity	NPC291820
0.8318	Intermediate Similarity	NPC122816
0.83	Intermediate Similarity	NPC329842
0.8273	Intermediate Similarity	NPC470063
0.8269	Intermediate Similarity	NPC251680
0.8257	Intermediate Similarity	NPC177047
0.8252	Intermediate Similarity	NPC477719
0.8252	Intermediate Similarity	NPC477718
0.8252	Intermediate Similarity	NPC210337
0.8246	Intermediate Similarity	NPC107607
0.8241	Intermediate Similarity	NPC88701
0.8224	Intermediate Similarity	NPC51719
0.8214	Intermediate Similarity	NPC106228
0.8214	Intermediate Similarity	NPC196931
0.8214	Intermediate Similarity	NPC138372
0.8208	Intermediate Similarity	NPC45897
0.8208	Intermediate Similarity	NPC112009
0.8208	Intermediate Similarity	NPC473523
0.8205	Intermediate Similarity	NPC469750
0.8205	Intermediate Similarity	NPC250556
0.819	Intermediate Similarity	NPC11974
0.819	Intermediate Similarity	NPC475617
0.8173	Intermediate Similarity	NPC218107
0.8173	Intermediate Similarity	NPC325229
0.8173	Intermediate Similarity	NPC476895
0.8173	Intermediate Similarity	NPC275086
0.8158	Intermediate Similarity	NPC278681
0.8155	Intermediate Similarity	NPC88009
0.8142	Intermediate Similarity	NPC185287
0.8137	Intermediate Similarity	NPC201725
0.8136	Intermediate Similarity	NPC179412
0.8136	Intermediate Similarity	NPC469757
0.8136	Intermediate Similarity	NPC329784
0.8136	Intermediate Similarity	NPC146456
0.8136	Intermediate Similarity	NPC240070
0.8136	Intermediate Similarity	NPC471356
0.8136	Intermediate Similarity	NPC471357
0.8136	Intermediate Similarity	NPC117702
0.8131	Intermediate Similarity	NPC152966
0.8131	Intermediate Similarity	NPC473543
0.8095	Intermediate Similarity	NPC476767
0.8095	Intermediate Similarity	NPC230546
0.8095	Intermediate Similarity	NPC473510
0.8095	Intermediate Similarity	NPC477721
0.8095	Intermediate Similarity	NPC324841
0.8095	Intermediate Similarity	NPC477716
0.8087	Intermediate Similarity	NPC112936
0.8087	Intermediate Similarity	NPC470312
0.8077	Intermediate Similarity	NPC476893
0.8077	Intermediate Similarity	NPC51499
0.8073	Intermediate Similarity	NPC304276
0.8073	Intermediate Similarity	NPC137462
0.807	Intermediate Similarity	NPC16701
0.8058	Intermediate Similarity	NPC329435
0.8058	Intermediate Similarity	NPC472441
0.8058	Intermediate Similarity	NPC276110
0.8056	Intermediate Similarity	NPC85670
0.8053	Intermediate Similarity	NPC469794
0.8053	Intermediate Similarity	NPC72772
0.8039	Intermediate Similarity	NPC53555
0.8039	Intermediate Similarity	NPC98193
0.8039	Intermediate Similarity	NPC472812
0.8037	Intermediate Similarity	NPC474124
0.8037	Intermediate Similarity	NPC180204
0.802	Intermediate Similarity	NPC78973
0.8019	Intermediate Similarity	NPC476896
0.8019	Intermediate Similarity	NPC477717
0.8018	Intermediate Similarity	NPC470076
0.8017	Intermediate Similarity	NPC42670
0.8017	Intermediate Similarity	NPC19124
0.8	Intermediate Similarity	NPC469751
0.8	Intermediate Similarity	NPC469752
0.8	Intermediate Similarity	NPC213761
0.8	Intermediate Similarity	NPC471358
0.8	Intermediate Similarity	NPC473570
0.8	Intermediate Similarity	NPC251866
0.8	Intermediate Similarity	NPC89514
0.8	Intermediate Similarity	NPC180079
0.8	Intermediate Similarity	NPC10823
0.8	Intermediate Similarity	NPC9674
0.8	Intermediate Similarity	NPC472810
0.8	Intermediate Similarity	NPC140092
0.8	Intermediate Similarity	NPC6108
0.8	Intermediate Similarity	NPC469755
0.8	Intermediate Similarity	NPC232785
0.8	Intermediate Similarity	NPC276838
0.8	Intermediate Similarity	NPC70542
0.8	Intermediate Similarity	NPC219085
0.8	Intermediate Similarity	NPC471359
0.8	Intermediate Similarity	NPC35171
0.8	Intermediate Similarity	NPC471361
0.8	Intermediate Similarity	NPC284406
0.8	Intermediate Similarity	NPC471360
0.8	Intermediate Similarity	NPC125077
0.8	Intermediate Similarity	NPC9499
0.8	Intermediate Similarity	NPC469754
0.8	Intermediate Similarity	NPC471352

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 NPC472820 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1527
0.2-0.3	4042
0.3-0.4	2329
0.4-0.5	592
0.5-0.6	218
0.6-0.7	206
0.7-0.8	48
0.8-0.85	13
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8727	High Similarity	NPD7327	Approved
0.8727	High Similarity	NPD7328	Approved
0.8649	High Similarity	NPD7516	Approved
0.8571	High Similarity	NPD8377	Approved
0.8571	High Similarity	NPD8294	Approved
0.8496	Intermediate Similarity	NPD8296	Approved
0.8496	Intermediate Similarity	NPD8378	Approved
0.8496	Intermediate Similarity	NPD8033	Approved
0.8496	Intermediate Similarity	NPD8380	Approved
0.8496	Intermediate Similarity	NPD8335	Approved
0.8496	Intermediate Similarity	NPD8379	Approved
0.8269	Intermediate Similarity	NPD7640	Approved
0.8269	Intermediate Similarity	NPD7639	Approved
0.8205	Intermediate Similarity	NPD7507	Approved
0.8173	Intermediate Similarity	NPD7638	Approved
0.8	Intermediate Similarity	NPD7319	Approved
0.7863	Intermediate Similarity	NPD7503	Approved
0.7664	Intermediate Similarity	NPD4225	Approved
0.7615	Intermediate Similarity	NPD7632	Discontinued
0.7589	Intermediate Similarity	NPD6686	Approved
0.7521	Intermediate Similarity	NPD7115	Discovery
0.7404	Intermediate Similarity	NPD6051	Approved
0.7377	Intermediate Similarity	NPD7492	Approved
0.7368	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6412	Phase 2
0.7339	Intermediate Similarity	NPD7736	Approved
0.7333	Intermediate Similarity	NPD6059	Approved
0.7333	Intermediate Similarity	NPD6054	Approved
0.7333	Intermediate Similarity	NPD6319	Approved
0.7317	Intermediate Similarity	NPD6616	Approved
0.7281	Intermediate Similarity	NPD7320	Approved
0.7273	Intermediate Similarity	NPD6015	Approved
0.7273	Intermediate Similarity	NPD6016	Approved
0.7265	Intermediate Similarity	NPD8133	Approved
0.7265	Intermediate Similarity	NPD4632	Approved
0.7258	Intermediate Similarity	NPD7078	Approved
0.7258	Intermediate Similarity	NPD8293	Discontinued
0.7257	Intermediate Similarity	NPD7128	Approved
0.7257	Intermediate Similarity	NPD6675	Approved
0.7257	Intermediate Similarity	NPD6402	Approved
0.7257	Intermediate Similarity	NPD5739	Approved
0.7248	Intermediate Similarity	NPD6084	Phase 2
0.7248	Intermediate Similarity	NPD6083	Phase 2
0.7227	Intermediate Similarity	NPD6009	Approved
0.7213	Intermediate Similarity	NPD6370	Approved
0.7213	Intermediate Similarity	NPD5988	Approved
0.7212	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7524	Approved
0.7193	Intermediate Similarity	NPD5697	Approved
0.7193	Intermediate Similarity	NPD5701	Approved
0.7179	Intermediate Similarity	NPD6882	Approved
0.7179	Intermediate Similarity	NPD8297	Approved
0.713	Intermediate Similarity	NPD6881	Approved
0.713	Intermediate Similarity	NPD6899	Approved
0.7069	Intermediate Similarity	NPD6373	Approved
0.7069	Intermediate Similarity	NPD6372	Approved
0.7069	Intermediate Similarity	NPD6012	Approved
0.7069	Intermediate Similarity	NPD6014	Approved
0.7069	Intermediate Similarity	NPD6013	Approved
0.7064	Intermediate Similarity	NPD5695	Phase 3
0.7054	Intermediate Similarity	NPD5344	Discontinued
0.7034	Intermediate Similarity	NPD6053	Discontinued
0.703	Intermediate Similarity	NPD7525	Registered
0.7027	Intermediate Similarity	NPD5696	Approved
0.7009	Intermediate Similarity	NPD4634	Approved
0.7009	Intermediate Similarity	NPD6883	Approved
0.7009	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7102	Approved
0.7009	Intermediate Similarity	NPD7290	Approved
0.6991	Remote Similarity	NPD5211	Phase 2
0.699	Remote Similarity	NPD6695	Phase 3
0.6983	Remote Similarity	NPD6011	Approved
0.6957	Remote Similarity	NPD6008	Approved
0.6949	Remote Similarity	NPD6869	Approved
0.6949	Remote Similarity	NPD6649	Approved
0.6949	Remote Similarity	NPD6617	Approved
0.6949	Remote Similarity	NPD6847	Approved
0.6949	Remote Similarity	NPD6650	Approved
0.6949	Remote Similarity	NPD8130	Phase 1
0.6944	Remote Similarity	NPD7637	Suspended
0.6944	Remote Similarity	NPD5693	Phase 1
0.6937	Remote Similarity	NPD4755	Approved
0.6934	Remote Similarity	NPD7625	Phase 1
0.6923	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD4753	Phase 2
0.6881	Remote Similarity	NPD4202	Approved
0.687	Remote Similarity	NPD5141	Approved
0.6855	Remote Similarity	NPD5983	Phase 2
0.6822	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6903	Approved
0.6814	Remote Similarity	NPD5285	Approved
0.6814	Remote Similarity	NPD5286	Approved
0.6814	Remote Similarity	NPD4700	Approved
0.6814	Remote Similarity	NPD4696	Approved
0.6807	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6033	Approved
0.6792	Remote Similarity	NPD7334	Approved
0.6792	Remote Similarity	NPD7146	Approved
0.6792	Remote Similarity	NPD6684	Approved
0.6792	Remote Similarity	NPD5330	Approved
0.6792	Remote Similarity	NPD7521	Approved
0.6792	Remote Similarity	NPD6409	Approved
0.6765	Remote Similarity	NPD4195	Approved
0.6762	Remote Similarity	NPD3666	Approved
0.6762	Remote Similarity	NPD3133	Approved
0.6762	Remote Similarity	NPD3665	Phase 1
0.6757	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD4159	Approved
0.6752	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7604	Phase 2
0.6746	Remote Similarity	NPD6067	Discontinued
0.6731	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7750	Discontinued
0.6727	Remote Similarity	NPD6399	Phase 3
0.6723	Remote Similarity	NPD6371	Approved
0.6721	Remote Similarity	NPD6274	Approved
0.6699	Remote Similarity	NPD6931	Approved
0.6699	Remote Similarity	NPD6930	Phase 2
0.6696	Remote Similarity	NPD5225	Approved
0.6696	Remote Similarity	NPD5224	Approved
0.6696	Remote Similarity	NPD5226	Approved
0.6696	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD7748	Approved
0.6641	Remote Similarity	NPD6336	Discontinued
0.6638	Remote Similarity	NPD5174	Approved
0.6638	Remote Similarity	NPD5175	Approved
0.6636	Remote Similarity	NPD7515	Phase 2
0.6636	Remote Similarity	NPD3618	Phase 1
0.6609	Remote Similarity	NPD5223	Approved
0.6607	Remote Similarity	NPD5210	Approved
0.6607	Remote Similarity	NPD4629	Approved
0.6606	Remote Similarity	NPD6904	Approved
0.6606	Remote Similarity	NPD6673	Approved
0.6606	Remote Similarity	NPD5328	Approved
0.6606	Remote Similarity	NPD6080	Approved
0.6602	Remote Similarity	NPD6929	Approved
0.6571	Remote Similarity	NPD4221	Approved
0.6571	Remote Similarity	NPD4223	Phase 3
0.6565	Remote Similarity	NPD5956	Approved
0.656	Remote Similarity	NPD7100	Approved
0.656	Remote Similarity	NPD7101	Approved
0.6542	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7514	Phase 3
0.6535	Remote Similarity	NPD6942	Approved
0.6535	Remote Similarity	NPD7339	Approved
0.6532	Remote Similarity	NPD6317	Approved
0.6525	Remote Similarity	NPD4768	Approved
0.6525	Remote Similarity	NPD4767	Approved
0.6518	Remote Similarity	NPD6001	Approved
0.6514	Remote Similarity	NPD5737	Approved
0.6514	Remote Similarity	NPD6672	Approved
0.6514	Remote Similarity	NPD5208	Approved
0.6496	Remote Similarity	NPD4754	Approved
0.6491	Remote Similarity	NPD7902	Approved
0.6486	Remote Similarity	NPD8034	Phase 2
0.6486	Remote Similarity	NPD5281	Approved
0.6486	Remote Similarity	NPD8035	Phase 2
0.6486	Remote Similarity	NPD6079	Approved
0.6486	Remote Similarity	NPD7087	Discontinued
0.6486	Remote Similarity	NPD5284	Approved
0.6484	Remote Similarity	NPD8328	Phase 3
0.648	Remote Similarity	NPD6314	Approved
0.648	Remote Similarity	NPD6335	Approved
0.648	Remote Similarity	NPD6313	Approved
0.6471	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6933	Approved
0.6457	Remote Similarity	NPD6908	Approved
0.6457	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6909	Approved
0.6449	Remote Similarity	NPD4786	Approved
0.6449	Remote Similarity	NPD4197	Approved
0.6442	Remote Similarity	NPD7645	Phase 2
0.6435	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8171	Discontinued
0.6417	Remote Similarity	NPD5128	Approved
0.6417	Remote Similarity	NPD4729	Approved
0.6417	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD4730	Approved
0.6415	Remote Similarity	NPD3667	Approved
0.6408	Remote Similarity	NPD5776	Phase 2
0.6408	Remote Similarity	NPD6925	Approved
0.6404	Remote Similarity	NPD5222	Approved
0.6404	Remote Similarity	NPD5221	Approved
0.6404	Remote Similarity	NPD4697	Phase 3
0.6404	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4243	Approved
0.6396	Remote Similarity	NPD7838	Discovery
0.6396	Remote Similarity	NPD5207	Approved
0.6396	Remote Similarity	NPD46	Approved
0.6396	Remote Similarity	NPD5692	Phase 3
0.6396	Remote Similarity	NPD6698	Approved
0.6396	Remote Similarity	NPD5785	Approved
0.6389	Remote Similarity	NPD6893	Approved
0.6389	Remote Similarity	NPD5329	Approved
0.6381	Remote Similarity	NPD7332	Phase 2

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