NPASS Compound

Structure

NPC177343 OpenBabel07101718312D 27 29 0 0 1 0 0 0 0 0999 V2000 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.8660 0.0000 C 0 0 0 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 -0.7321 1.0000 0.0000 C 0 0 0 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 -3.4641 -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 -2.5981 -1.5000 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 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 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 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 1.8660 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 13 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 12 1 1 1 0 0 0 12 15 1 0 0 0 0 12 26 1 0 0 0 0 13 19 1 6 0 0 0 14 20 1 6 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 6 0 0 0 16 17 1 0 0 0 0 16 23 1 1 0 0 0 17 18 1 0 0 0 0 17 24 1 1 0 0 0 18 26 1 0 0 0 0 18 27 1 6 0 0 0 19 27 1 0 0 0 0 20 4 1 6 0 0 0 21 5 1 6 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.27
Volume:	398.844
LogP:	2.895
LogD:	3.092
LogS:	-3.582
# Rotatable Bonds:	3
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.592
Synthetic Accessibility Score:	4.78
Fsp3:	1.0
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:	-4.799
MDCK Permeability:	9.490627235209104e-06
Pgp-inhibitor:	0.061
Pgp-substrate:	0.274
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.093

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	91.7300033569336%
Volume Distribution (VD):	0.847
Pgp-substrate:	5.724592208862305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.602
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.874
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.303
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.209
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.07

ADMET: Excretion

Clearance (CL):	1.84
Half-life (T1/2):	0.575

ADMET: Toxicity

hERG Blockers:	0.074
Human Hepatotoxicity (H-HT):	0.047
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.526
Carcinogencity:	0.023
Eye Corrosion:	0.281
Eye Irritation:	0.843
Respiratory Toxicity:	0.837

Download Data

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

Natural Product: NPC177343

Natural Product ID:	NPC177343
*Common Name:**	Cryptomeridiol 11-Alpha-L-Rhamnoside
IUPAC Name:	(2S,3R,4R,5R,6S)-2-[2-[(2R,4aR,8R,8aR)-8-hydroxy-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]propan-2-yloxy]-6-methyloxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	HUSBLOAZNQURFJ-YOYCCLINSA-N
Standard InCHI:	InChI=1S/C21H38O6/c1-12-15(22)16(23)17(24)18(26-12)27-19(2,3)13-7-10-20(4)8-6-9-21(5,25)14(20)11-13/h12-18,22-25H,6-11H2,1-5H3/t12-,13+,14+,15-,16+,17+,18-,20+,21+/m0/s1
SMILES:	C[C@@H]1O[C@@H](OC([C@@H]2CC[C@@]3([C@@H](C2)[C@](C)(O)CCC3)C)(C)C)[C@@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477719
PubChem CID:	11731806
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

*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
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	fruits	n.a.	n.a.	PMID[11374955]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21504145]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	flower buds	Thailand	n.a.	PMID[24601675]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9348	Cananga odorata	Species	Annonaceae	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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	0.01	ug.mL-1	PMID[570835]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.36	ug.mL-1	PMID[570835]

☑ 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 NPC177343 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	535
0.1-0.2	4365
0.2-0.3	11472
0.3-0.4	12503
0.4-0.5	5697
0.5-0.6	4496
0.6-0.7	2920
0.7-0.8	643
0.8-0.85	53
0.85-0.9	11
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9351	High Similarity	NPC241959
0.92	High Similarity	NPC272841
0.9178	High Similarity	NPC308489
0.9114	High Similarity	NPC290612
0.9	High Similarity	NPC471410
0.9	High Similarity	NPC471411
0.8889	High Similarity	NPC140446
0.8889	High Similarity	NPC43912
0.8767	High Similarity	NPC471879
0.8684	High Similarity	NPC107963
0.8675	High Similarity	NPC82955
0.8675	High Similarity	NPC131466
0.8667	High Similarity	NPC166250
0.8571	High Similarity	NPC261990
0.8571	High Similarity	NPC279329
0.8571	High Similarity	NPC474249
0.8554	High Similarity	NPC281004
0.8519	High Similarity	NPC18953
0.8519	High Similarity	NPC474156
0.8481	Intermediate Similarity	NPC186588
0.8471	Intermediate Similarity	NPC307167
0.8471	Intermediate Similarity	NPC210759
0.8471	Intermediate Similarity	NPC36372
0.8471	Intermediate Similarity	NPC293609
0.8471	Intermediate Similarity	NPC229801
0.8462	Intermediate Similarity	NPC477577
0.8452	Intermediate Similarity	NPC102725
0.8452	Intermediate Similarity	NPC473472
0.8434	Intermediate Similarity	NPC472396
0.8421	Intermediate Similarity	NPC209666
0.8421	Intermediate Similarity	NPC53868
0.8421	Intermediate Similarity	NPC31046
0.8421	Intermediate Similarity	NPC200167
0.8372	Intermediate Similarity	NPC277774
0.8372	Intermediate Similarity	NPC171741
0.8372	Intermediate Similarity	NPC470623
0.8372	Intermediate Similarity	NPC18724
0.8372	Intermediate Similarity	NPC311246
0.8372	Intermediate Similarity	NPC323231
0.8372	Intermediate Similarity	NPC224003
0.8372	Intermediate Similarity	NPC167644
0.8353	Intermediate Similarity	NPC473542
0.8353	Intermediate Similarity	NPC223143
0.8353	Intermediate Similarity	NPC65550
0.8313	Intermediate Similarity	NPC268633
0.8312	Intermediate Similarity	NPC472950
0.8312	Intermediate Similarity	NPC472952
0.8293	Intermediate Similarity	NPC166279
0.8276	Intermediate Similarity	NPC30687
0.8276	Intermediate Similarity	NPC191915
0.8276	Intermediate Similarity	NPC477224
0.8276	Intermediate Similarity	NPC148593
0.8276	Intermediate Similarity	NPC3538
0.8276	Intermediate Similarity	NPC473503
0.8276	Intermediate Similarity	NPC309866
0.8276	Intermediate Similarity	NPC252253
0.8276	Intermediate Similarity	NPC151214
0.8276	Intermediate Similarity	NPC267238
0.8276	Intermediate Similarity	NPC305418
0.8276	Intermediate Similarity	NPC471373
0.8276	Intermediate Similarity	NPC253611
0.8276	Intermediate Similarity	NPC77717
0.8276	Intermediate Similarity	NPC113500
0.8276	Intermediate Similarity	NPC45959
0.8276	Intermediate Similarity	NPC175
0.8256	Intermediate Similarity	NPC59006
0.8256	Intermediate Similarity	NPC289361
0.8256	Intermediate Similarity	NPC204881
0.8256	Intermediate Similarity	NPC473830
0.8256	Intermediate Similarity	NPC473637
0.8256	Intermediate Similarity	NPC149966
0.8256	Intermediate Similarity	NPC5632
0.8256	Intermediate Similarity	NPC476668
0.8235	Intermediate Similarity	NPC20822
0.8214	Intermediate Similarity	NPC210658
0.8214	Intermediate Similarity	NPC45833
0.8214	Intermediate Similarity	NPC62202
0.8214	Intermediate Similarity	NPC110365
0.8214	Intermediate Similarity	NPC213658
0.8214	Intermediate Similarity	NPC161928
0.8182	Intermediate Similarity	NPC473065
0.8182	Intermediate Similarity	NPC471425
0.8182	Intermediate Similarity	NPC469710
0.8182	Intermediate Similarity	NPC189575
0.8182	Intermediate Similarity	NPC473067
0.8182	Intermediate Similarity	NPC471429
0.8182	Intermediate Similarity	NPC473064
0.8182	Intermediate Similarity	NPC57964
0.8182	Intermediate Similarity	NPC471424
0.8182	Intermediate Similarity	NPC92196
0.8182	Intermediate Similarity	NPC94582
0.8182	Intermediate Similarity	NPC477494
0.8182	Intermediate Similarity	NPC205129
0.8182	Intermediate Similarity	NPC106701
0.8171	Intermediate Similarity	NPC474253
0.8171	Intermediate Similarity	NPC213737
0.8171	Intermediate Similarity	NPC474346
0.8171	Intermediate Similarity	NPC475820
0.8171	Intermediate Similarity	NPC470070
0.8171	Intermediate Similarity	NPC474284
0.8161	Intermediate Similarity	NPC137004
0.8161	Intermediate Similarity	NPC144790
0.8161	Intermediate Similarity	NPC88962
0.8161	Intermediate Similarity	NPC476669
0.8161	Intermediate Similarity	NPC172838
0.8161	Intermediate Similarity	NPC473726
0.8161	Intermediate Similarity	NPC149400
0.8133	Intermediate Similarity	NPC470833
0.8118	Intermediate Similarity	NPC128475
0.8118	Intermediate Similarity	NPC470872
0.8095	Intermediate Similarity	NPC107603
0.8095	Intermediate Similarity	NPC471240
0.809	Intermediate Similarity	NPC139271
0.809	Intermediate Similarity	NPC304011
0.809	Intermediate Similarity	NPC252056
0.809	Intermediate Similarity	NPC473287
0.809	Intermediate Similarity	NPC472989
0.809	Intermediate Similarity	NPC476510
0.809	Intermediate Similarity	NPC238796
0.809	Intermediate Similarity	NPC203434
0.809	Intermediate Similarity	NPC142264
0.809	Intermediate Similarity	NPC90583
0.809	Intermediate Similarity	NPC237071
0.8068	Intermediate Similarity	NPC312678
0.8068	Intermediate Similarity	NPC24960
0.8068	Intermediate Similarity	NPC253268
0.8068	Intermediate Similarity	NPC475325
0.8068	Intermediate Similarity	NPC174024
0.8068	Intermediate Similarity	NPC305160
0.8068	Intermediate Similarity	NPC179859
0.8068	Intermediate Similarity	NPC475436
0.8068	Intermediate Similarity	NPC473851
0.8068	Intermediate Similarity	NPC473774
0.8068	Intermediate Similarity	NPC291547
0.8068	Intermediate Similarity	NPC131693
0.8049	Intermediate Similarity	NPC208912
0.8049	Intermediate Similarity	NPC2096
0.8049	Intermediate Similarity	NPC470611
0.8026	Intermediate Similarity	NPC29005
0.8026	Intermediate Similarity	NPC5209
0.8026	Intermediate Similarity	NPC51956
0.8025	Intermediate Similarity	NPC471216
0.8025	Intermediate Similarity	NPC471217
0.8025	Intermediate Similarity	NPC472943
0.8025	Intermediate Similarity	NPC472951
0.8023	Intermediate Similarity	NPC228059
0.8	Intermediate Similarity	NPC477223
0.8	Intermediate Similarity	NPC233649
0.8	Intermediate Similarity	NPC477222
0.8	Intermediate Similarity	NPC470028
0.7978	Intermediate Similarity	NPC474399
0.7976	Intermediate Similarity	NPC235402
0.7976	Intermediate Similarity	NPC232044
0.7976	Intermediate Similarity	NPC273290
0.7955	Intermediate Similarity	NPC48339
0.7955	Intermediate Similarity	NPC475307
0.7955	Intermediate Similarity	NPC477451
0.7955	Intermediate Similarity	NPC177834
0.7955	Intermediate Similarity	NPC477547
0.7955	Intermediate Similarity	NPC141769
0.7955	Intermediate Similarity	NPC234352
0.7955	Intermediate Similarity	NPC249204
0.7955	Intermediate Similarity	NPC325828
0.7955	Intermediate Similarity	NPC297348
0.7955	Intermediate Similarity	NPC250393
0.7949	Intermediate Similarity	NPC470151
0.7927	Intermediate Similarity	NPC71541
0.7922	Intermediate Similarity	NPC157777
0.7922	Intermediate Similarity	NPC131506
0.7912	Intermediate Similarity	NPC209798
0.7912	Intermediate Similarity	NPC473638
0.7912	Intermediate Similarity	NPC471375
0.7912	Intermediate Similarity	NPC471374
0.7901	Intermediate Similarity	NPC477282
0.7901	Intermediate Similarity	NPC81074
0.7889	Intermediate Similarity	NPC296936
0.7889	Intermediate Similarity	NPC121453
0.7875	Intermediate Similarity	NPC474574
0.7875	Intermediate Similarity	NPC133596
0.7875	Intermediate Similarity	NPC64081
0.7875	Intermediate Similarity	NPC188793
0.7875	Intermediate Similarity	NPC11907
0.7867	Intermediate Similarity	NPC477761
0.7867	Intermediate Similarity	NPC179823
0.7867	Intermediate Similarity	NPC477758
0.7867	Intermediate Similarity	NPC477759
0.7867	Intermediate Similarity	NPC477760
0.7867	Intermediate Similarity	NPC477754
0.7865	Intermediate Similarity	NPC291203
0.7865	Intermediate Similarity	NPC72817
0.7865	Intermediate Similarity	NPC477927
0.7865	Intermediate Similarity	NPC222731
0.7865	Intermediate Similarity	NPC264101
0.7865	Intermediate Similarity	NPC211238
0.7865	Intermediate Similarity	NPC294686
0.7865	Intermediate Similarity	NPC471464
0.7865	Intermediate Similarity	NPC217205
0.7857	Intermediate Similarity	NPC227260
0.7841	Intermediate Similarity	NPC302584
0.7841	Intermediate Similarity	NPC48463

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 NPC177343 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	562
0.1-0.2	4244
0.2-0.3	2892
0.3-0.4	838
0.4-0.5	331
0.5-0.6	216
0.6-0.7	55
0.7-0.8	10
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8421	Intermediate Similarity	NPD1810	Approved
0.8421	Intermediate Similarity	NPD1811	Approved
0.8026	Intermediate Similarity	NPD2687	Approved
0.8026	Intermediate Similarity	NPD2254	Approved
0.8026	Intermediate Similarity	NPD2686	Approved
0.7955	Intermediate Similarity	NPD8171	Discontinued
0.759	Intermediate Similarity	NPD6928	Phase 2
0.7529	Intermediate Similarity	NPD3669	Approved
0.7529	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD371	Approved
0.7436	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7532	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1779	Approved
0.6897	Remote Similarity	NPD1780	Approved
0.6832	Remote Similarity	NPD6412	Phase 2
0.6762	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6606	Remote Similarity	NPD7516	Approved
0.6602	Remote Similarity	NPD6686	Approved
0.6574	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6697	Approved
0.6552	Remote Similarity	NPD6115	Approved
0.6552	Remote Similarity	NPD6118	Approved
0.6552	Remote Similarity	NPD6114	Approved
0.6545	Remote Similarity	NPD8294	Approved
0.6545	Remote Similarity	NPD8377	Approved
0.6495	Remote Similarity	NPD7991	Discontinued
0.6486	Remote Similarity	NPD7503	Approved
0.6486	Remote Similarity	NPD8335	Approved
0.6486	Remote Similarity	NPD8378	Approved
0.6486	Remote Similarity	NPD8380	Approved
0.6486	Remote Similarity	NPD8033	Approved
0.6486	Remote Similarity	NPD8296	Approved
0.6486	Remote Similarity	NPD8379	Approved
0.6481	Remote Similarity	NPD6940	Discontinued
0.6442	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD2269	Approved
0.6437	Remote Similarity	NPD6116	Phase 1
0.641	Remote Similarity	NPD6123	Approved
0.6351	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD893	Approved
0.6351	Remote Similarity	NPD892	Phase 3
0.6351	Remote Similarity	NPD888	Phase 3
0.6351	Remote Similarity	NPD891	Phase 3
0.6322	Remote Similarity	NPD6117	Approved
0.6316	Remote Similarity	NPD2267	Suspended
0.631	Remote Similarity	NPD4787	Phase 1
0.6301	Remote Similarity	NPD904	Phase 3
0.6301	Remote Similarity	NPD905	Approved
0.6286	Remote Similarity	NPD8174	Phase 2
0.6261	Remote Similarity	NPD7507	Approved
0.6228	Remote Similarity	NPD8328	Phase 3
0.6222	Remote Similarity	NPD7525	Registered
0.6207	Remote Similarity	NPD3703	Phase 2
0.614	Remote Similarity	NPD6370	Approved
0.6133	Remote Similarity	NPD895	Approved
0.6133	Remote Similarity	NPD887	Approved
0.6133	Remote Similarity	NPD894	Approved
0.6133	Remote Similarity	NPD889	Approved
0.6111	Remote Similarity	NPD7645	Phase 2
0.6105	Remote Similarity	NPD7524	Approved
0.6102	Remote Similarity	NPD7319	Approved
0.6092	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD7346	Approved
0.6047	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD3702	Approved
0.6	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD384	Approved
0.5972	Remote Similarity	NPD385	Approved
0.5965	Remote Similarity	NPD6059	Approved
0.5965	Remote Similarity	NPD6054	Approved
0.5957	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD8293	Discontinued
0.593	Remote Similarity	NPD4245	Approved
0.593	Remote Similarity	NPD4244	Approved
0.5882	Remote Similarity	NPD7736	Approved
0.5851	Remote Similarity	NPD6695	Phase 3
0.5833	Remote Similarity	NPD8997	Approved
0.5833	Remote Similarity	NPD9000	Phase 3
0.5833	Remote Similarity	NPD8998	Phase 2
0.5833	Remote Similarity	NPD8999	Phase 3
0.5833	Remote Similarity	NPD8993	Phase 1
0.5825	Remote Similarity	NPD7638	Approved
0.5814	Remote Similarity	NPD3698	Phase 2
0.5812	Remote Similarity	NPD6067	Discontinued
0.581	Remote Similarity	NPD8139	Approved
0.581	Remote Similarity	NPD8083	Approved
0.581	Remote Similarity	NPD8082	Approved
0.581	Remote Similarity	NPD8086	Approved
0.581	Remote Similarity	NPD8084	Approved
0.581	Remote Similarity	NPD8085	Approved
0.581	Remote Similarity	NPD8138	Approved
0.5776	Remote Similarity	NPD6016	Approved
0.5776	Remote Similarity	NPD6921	Approved
0.5776	Remote Similarity	NPD6015	Approved
0.5769	Remote Similarity	NPD7640	Approved
0.5769	Remote Similarity	NPD7639	Approved
0.5763	Remote Similarity	NPD7492	Approved
0.5758	Remote Similarity	NPD3168	Discontinued
0.5755	Remote Similarity	NPD8276	Approved
0.5755	Remote Similarity	NPD8275	Approved
0.5747	Remote Similarity	NPD4789	Approved
0.5727	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD5988	Approved
0.5714	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6616	Approved
0.5702	Remote Similarity	NPD6009	Approved
0.5701	Remote Similarity	NPD3710	Phase 2
0.5701	Remote Similarity	NPD8081	Approved
0.57	Remote Similarity	NPD8034	Phase 2
0.57	Remote Similarity	NPD8035	Phase 2
0.5698	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD5360	Phase 3
0.5682	Remote Similarity	NPD5777	Approved
0.5676	Remote Similarity	NPD8966	Approved
0.5676	Remote Similarity	NPD8965	Approved
0.5667	Remote Similarity	NPD7078	Approved
0.566	Remote Similarity	NPD7632	Discontinued
0.5648	Remote Similarity	NPD8393	Approved
0.5625	Remote Similarity	NPD6882	Approved
0.5616	Remote Similarity	NPD388	Approved
0.5616	Remote Similarity	NPD386	Approved
0.5612	Remote Similarity	NPD7750	Discontinued
0.5604	Remote Similarity	NPD6933	Approved
0.56	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.56	Remote Similarity	NPD6700	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