NPASS Compound

Structure

NPC473871 OpenBabel07101719522D 35 38 0 0 1 0 0 0 0 0999 V2000 0.1302 -1.2012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3620 2.4274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7124 0.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9266 1.6618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2409 0.7414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6091 0.4083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1890 3.0349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4761 3.6964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9726 2.0867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1845 1.2267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5467 3.4097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0432 1.8000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4009 2.1749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2551 0.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5790 -1.0651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2070 1.5416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9725 -0.7149 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4326 2.1407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8701 -0.0145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3303 2.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5086 1.4892 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1855 -0.7149 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6834 1.0282 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2868 0.9058 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1855 -0.0145 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2867 0.9294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5790 0.3356 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9725 -0.0145 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7197 2.8022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8701 -0.9871 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0278 -1.2012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5421 1.6015 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2162 1.1925 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0278 0.4717 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 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 20 1 0 0 0 0 14 32 1 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 28 1 1 0 0 0 18 29 2 0 0 0 0 18 33 1 0 0 0 0 19 30 2 0 0 0 0 19 34 1 0 0 0 0 21 16 1 6 0 0 0 21 24 1 0 0 0 0 21 26 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 1 0 0 0 23 27 1 6 0 0 0 23 32 1 0 0 0 0 24 28 1 1 0 0 0 24 33 1 0 0 0 0 25 27 1 1 0 0 0 25 34 1 0 0 0 0 26 35 1 0 0 0 0 27 28 1 6 0 0 0 28 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.26
Volume:	504.331
LogP:	3.559
LogD:	3.156
LogS:	-4.381
# Rotatable Bonds:	8
TPSA:	91.29
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.61
Synthetic Accessibility Score:	5.89
Fsp3:	0.643
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:	-5.042
MDCK Permeability:	2.4471464712405577e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.939
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.63

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.713
Plasma Protein Binding (PPB):	81.45182800292969%
Volume Distribution (VD):	1.481
Pgp-substrate:	18.442821502685547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.085
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.333
CYP2C9-inhibitor:	0.422
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.08
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.583
CYP3A4-substrate:	0.525

ADMET: Excretion

Clearance (CL):	3.437
Half-life (T1/2):	0.758

ADMET: Toxicity

hERG Blockers:	0.884
Human Hepatotoxicity (H-HT):	0.974
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.107
Rat Oral Acute Toxicity:	0.259
Maximum Recommended Daily Dose:	0.217
Skin Sensitization:	0.467
Carcinogencity:	0.21
Eye Corrosion:	0.007
Eye Irritation:	0.133
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC473871

Natural Product ID:	NPC473871
*Common Name:**	PRXSAUGKOVQAPK-ARTQGJCPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PRXSAUGKOVQAPK-ARTQGJCPSA-N
Standard InCHI:	InChI=1S/C28H38O7/c1-17-15-22(31)25(34-19(3)30)27(6)23(32-14-10-13-20-11-8-7-9-12-20)16-21-24(33-18(2)29)28(17,27)35-26(21,4)5/h7-13,17,21-25,31H,14-16H2,1-6H3/b13-10+/t17-,21-,22+,23+,24-,25+,27-,28-/m1/s1
SMILES:	CC1CC(C(C2(C13C(C(CC2OCC=CC4=CC=CC=C4)C(O3)(C)C)OC(=O)C)C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453840
PubChem CID:	44561262
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

*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
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170672]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[11809076]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[18507472]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23421714]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27791375]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	Activity	<	50.0	%	PMID[454307]

☑ 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 NPC473871 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	209
0.1-0.2	930
0.2-0.3	2131
0.3-0.4	4903
0.4-0.5	8655
0.5-0.6	17445
0.6-0.7	7475
0.7-0.8	738
0.8-0.85	150
0.85-0.9	30
0.9-0.95	12
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473870
0.9913	High Similarity	NPC473889
0.9746	High Similarity	NPC470158
0.9746	High Similarity	NPC475933
0.9664	High Similarity	NPC476971
0.9664	High Similarity	NPC476972
0.958	High Similarity	NPC476970
0.9565	High Similarity	NPC473860
0.9322	High Similarity	NPC311175
0.9322	High Similarity	NPC37641
0.9274	High Similarity	NPC476976
0.9244	High Similarity	NPC70973
0.9217	High Similarity	NPC473869
0.9194	High Similarity	NPC476977
0.9016	High Similarity	NPC473083
0.9016	High Similarity	NPC114927
0.8983	High Similarity	NPC84129
0.8943	High Similarity	NPC473110
0.8943	High Similarity	NPC473111
0.8943	High Similarity	NPC473082
0.8779	High Similarity	NPC100913
0.8779	High Similarity	NPC275592
0.8712	High Similarity	NPC97947
0.8712	High Similarity	NPC291599
0.8712	High Similarity	NPC87448
0.8712	High Similarity	NPC27377
0.8712	High Similarity	NPC118080
0.8712	High Similarity	NPC41481
0.8712	High Similarity	NPC472576
0.871	High Similarity	NPC471758
0.864	High Similarity	NPC45821
0.8636	High Similarity	NPC90614
0.8636	High Similarity	NPC171207
0.8636	High Similarity	NPC97667
0.8583	High Similarity	NPC93632
0.8571	High Similarity	NPC16912
0.8548	High Similarity	NPC12016
0.8519	High Similarity	NPC241951
0.8519	High Similarity	NPC470152
0.8519	High Similarity	NPC475759
0.8519	High Similarity	NPC475122
0.8504	High Similarity	NPC58061
0.848	Intermediate Similarity	NPC472373
0.8456	Intermediate Similarity	NPC174982
0.8456	Intermediate Similarity	NPC70403
0.8456	Intermediate Similarity	NPC470159
0.8456	Intermediate Similarity	NPC96903
0.8456	Intermediate Similarity	NPC158663
0.8456	Intermediate Similarity	NPC470157
0.8456	Intermediate Similarity	NPC184817
0.8456	Intermediate Similarity	NPC171525
0.8456	Intermediate Similarity	NPC476973
0.8456	Intermediate Similarity	NPC177940
0.8456	Intermediate Similarity	NPC469349
0.8456	Intermediate Similarity	NPC471104
0.8456	Intermediate Similarity	NPC29704
0.8456	Intermediate Similarity	NPC473088
0.8456	Intermediate Similarity	NPC472568
0.8456	Intermediate Similarity	NPC472571
0.8456	Intermediate Similarity	NPC200471
0.8456	Intermediate Similarity	NPC472572
0.8456	Intermediate Similarity	NPC472575
0.8444	Intermediate Similarity	NPC163087
0.843	Intermediate Similarity	NPC470820
0.8413	Intermediate Similarity	NPC284022
0.8397	Intermediate Similarity	NPC474608
0.8387	Intermediate Similarity	NPC300827
0.8387	Intermediate Similarity	NPC473439
0.8385	Intermediate Similarity	NPC80599
0.8382	Intermediate Similarity	NPC11685
0.8382	Intermediate Similarity	NPC163719
0.8382	Intermediate Similarity	NPC95265
0.8382	Intermediate Similarity	NPC188865
0.8382	Intermediate Similarity	NPC70716
0.8382	Intermediate Similarity	NPC125106
0.8382	Intermediate Similarity	NPC472570
0.8382	Intermediate Similarity	NPC476974
0.8382	Intermediate Similarity	NPC472573
0.8382	Intermediate Similarity	NPC95810
0.8382	Intermediate Similarity	NPC25768
0.8382	Intermediate Similarity	NPC472569
0.8382	Intermediate Similarity	NPC57628
0.8359	Intermediate Similarity	NPC230331
0.8358	Intermediate Similarity	NPC472547
0.8346	Intermediate Similarity	NPC39549
0.8333	Intermediate Similarity	NPC291638
0.8333	Intermediate Similarity	NPC66761
0.8333	Intermediate Similarity	NPC17877
0.8333	Intermediate Similarity	NPC470815
0.8333	Intermediate Similarity	NPC472577
0.8333	Intermediate Similarity	NPC195647
0.8321	Intermediate Similarity	NPC301946
0.8321	Intermediate Similarity	NPC277053
0.832	Intermediate Similarity	NPC475328
0.8281	Intermediate Similarity	NPC5486
0.8273	Intermediate Similarity	NPC476975
0.8273	Intermediate Similarity	NPC270590
0.8273	Intermediate Similarity	NPC473215
0.8273	Intermediate Similarity	NPC301556
0.8273	Intermediate Similarity	NPC266265
0.8273	Intermediate Similarity	NPC92293
0.8273	Intermediate Similarity	NPC471101
0.8271	Intermediate Similarity	NPC472551
0.8271	Intermediate Similarity	NPC472545
0.8261	Intermediate Similarity	NPC474935
0.8248	Intermediate Similarity	NPC80895
0.8248	Intermediate Similarity	NPC471912
0.8235	Intermediate Similarity	NPC34012
0.8235	Intermediate Similarity	NPC475513
0.8235	Intermediate Similarity	NPC473755
0.8214	Intermediate Similarity	NPC473214
0.8214	Intermediate Similarity	NPC470245
0.8209	Intermediate Similarity	NPC283375
0.8209	Intermediate Similarity	NPC183122
0.8203	Intermediate Similarity	NPC470816
0.8201	Intermediate Similarity	NPC281717
0.8189	Intermediate Similarity	NPC77691
0.8189	Intermediate Similarity	NPC307139
0.8188	Intermediate Similarity	NPC472556
0.8175	Intermediate Similarity	NPC91703
0.8175	Intermediate Similarity	NPC473749
0.8162	Intermediate Similarity	NPC325078
0.8162	Intermediate Similarity	NPC224491
0.8156	Intermediate Similarity	NPC471103
0.8156	Intermediate Similarity	NPC470153
0.8148	Intermediate Similarity	NPC210591
0.8148	Intermediate Similarity	NPC475652
0.8148	Intermediate Similarity	NPC214550
0.8145	Intermediate Similarity	NPC89324
0.8143	Intermediate Similarity	NPC474564
0.814	Intermediate Similarity	NPC190849
0.814	Intermediate Similarity	NPC171007
0.8116	Intermediate Similarity	NPC471139
0.8116	Intermediate Similarity	NPC38696
0.811	Intermediate Similarity	NPC182333
0.811	Intermediate Similarity	NPC273336
0.811	Intermediate Similarity	NPC108286
0.8102	Intermediate Similarity	NPC140021
0.8092	Intermediate Similarity	NPC147561
0.8092	Intermediate Similarity	NPC475138
0.8092	Intermediate Similarity	NPC473443
0.8088	Intermediate Similarity	NPC43241
0.8088	Intermediate Similarity	NPC4341
0.8088	Intermediate Similarity	NPC473613
0.8088	Intermediate Similarity	NPC473112
0.8088	Intermediate Similarity	NPC473081
0.8088	Intermediate Similarity	NPC473085
0.8088	Intermediate Similarity	NPC48017
0.8088	Intermediate Similarity	NPC184747
0.8088	Intermediate Similarity	NPC200592
0.8088	Intermediate Similarity	NPC147880
0.8088	Intermediate Similarity	NPC473758
0.8088	Intermediate Similarity	NPC473109
0.8088	Intermediate Similarity	NPC473060
0.8088	Intermediate Similarity	NPC476094
0.8088	Intermediate Similarity	NPC211137
0.8087	Intermediate Similarity	NPC266343
0.8085	Intermediate Similarity	NPC475447
0.8085	Intermediate Similarity	NPC476092
0.8085	Intermediate Similarity	NPC70236
0.8085	Intermediate Similarity	NPC475218
0.808	Intermediate Similarity	NPC470814
0.8043	Intermediate Similarity	NPC477894
0.8028	Intermediate Similarity	NPC51602
0.8015	Intermediate Similarity	NPC225103
0.8	Intermediate Similarity	NPC473602
0.8	Intermediate Similarity	NPC478263
0.8	Intermediate Similarity	NPC240115
0.7986	Intermediate Similarity	NPC34943
0.7986	Intermediate Similarity	NPC34066
0.7972	Intermediate Similarity	NPC472548
0.7972	Intermediate Similarity	NPC477905
0.7971	Intermediate Similarity	NPC472546
0.797	Intermediate Similarity	NPC209851
0.7958	Intermediate Similarity	NPC469448
0.7955	Intermediate Similarity	NPC472388
0.7943	Intermediate Similarity	NPC473760
0.7943	Intermediate Similarity	NPC217918
0.7939	Intermediate Similarity	NPC195224
0.7931	Intermediate Similarity	NPC106895
0.7929	Intermediate Similarity	NPC311825
0.7929	Intermediate Similarity	NPC92867
0.7929	Intermediate Similarity	NPC127857
0.7929	Intermediate Similarity	NPC478264
0.7926	Intermediate Similarity	NPC477893
0.7926	Intermediate Similarity	NPC477896
0.7914	Intermediate Similarity	NPC139067
0.7914	Intermediate Similarity	NPC475429
0.7914	Intermediate Similarity	NPC246480
0.7914	Intermediate Similarity	NPC270498
0.7914	Intermediate Similarity	NPC473673
0.7914	Intermediate Similarity	NPC147217
0.7914	Intermediate Similarity	NPC177340
0.7914	Intermediate Similarity	NPC191082
0.7903	Intermediate Similarity	NPC476476
0.7902	Intermediate Similarity	NPC469415
0.7895	Intermediate Similarity	NPC472418
0.7887	Intermediate Similarity	NPC250046
0.7887	Intermediate Similarity	NPC81698
0.7887	Intermediate Similarity	NPC60509

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 NPC473871 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	666
0.2-0.3	1371
0.3-0.4	3209
0.4-0.5	2233
0.5-0.6	1241
0.6-0.7	237
0.7-0.8	10
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7857	Intermediate Similarity	NPD7741	Discontinued
0.776	Intermediate Similarity	NPD4198	Discontinued
0.7734	Intermediate Similarity	NPD5126	Approved
0.7734	Intermediate Similarity	NPD5125	Phase 3
0.7606	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6685	Approved
0.7266	Intermediate Similarity	NPD2629	Approved
0.7266	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7236	Approved
0.7083	Intermediate Similarity	NPD5762	Approved
0.7083	Intermediate Similarity	NPD5763	Approved
0.7073	Intermediate Similarity	NPD5765	Approved
0.7054	Intermediate Similarity	NPD6010	Discontinued
0.705	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5736	Approved
0.7021	Intermediate Similarity	NPD4140	Approved
0.7007	Intermediate Similarity	NPD3094	Phase 2
0.6993	Remote Similarity	NPD37	Approved
0.6977	Remote Similarity	NPD6858	Approved
0.6977	Remote Similarity	NPD7094	Approved
0.697	Remote Similarity	NPD7516	Approved
0.6968	Remote Similarity	NPD4967	Phase 2
0.6968	Remote Similarity	NPD4965	Approved
0.6968	Remote Similarity	NPD4966	Approved
0.696	Remote Similarity	NPD5048	Discontinued
0.6957	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7239	Suspended
0.6935	Remote Similarity	NPD6647	Phase 2
0.6923	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD8407	Phase 2
0.6899	Remote Similarity	NPD6912	Phase 3
0.6894	Remote Similarity	NPD7327	Approved
0.6894	Remote Similarity	NPD7799	Discontinued
0.6894	Remote Similarity	NPD7328	Approved
0.6879	Remote Similarity	NPD6234	Discontinued
0.6853	Remote Similarity	NPD5735	Approved
0.6849	Remote Similarity	NPD7266	Discontinued
0.6838	Remote Similarity	NPD3092	Approved
0.6831	Remote Similarity	NPD7961	Discontinued
0.6831	Remote Similarity	NPD6663	Approved
0.6829	Remote Similarity	NPD8368	Discontinued
0.6829	Remote Similarity	NPD7798	Approved
0.6826	Remote Similarity	NPD8434	Phase 2
0.6824	Remote Similarity	NPD8166	Discontinued
0.6809	Remote Similarity	NPD7095	Approved
0.68	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD8127	Discontinued
0.679	Remote Similarity	NPD7228	Approved
0.6779	Remote Similarity	NPD6190	Approved
0.6774	Remote Similarity	NPD5344	Discontinued
0.6757	Remote Similarity	NPD6674	Discontinued
0.6748	Remote Similarity	NPD7638	Approved
0.6714	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7640	Approved
0.6694	Remote Similarity	NPD7639	Approved
0.6694	Remote Similarity	NPD6648	Approved
0.6691	Remote Similarity	NPD3095	Discontinued
0.6667	Remote Similarity	NPD3091	Approved
0.6667	Remote Similarity	NPD3620	Phase 2
0.6667	Remote Similarity	NPD4060	Phase 1
0.6667	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD8361	Approved
0.6647	Remote Similarity	NPD8360	Approved
0.6647	Remote Similarity	NPD8435	Approved
0.6645	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7097	Phase 1
0.6644	Remote Similarity	NPD41	Approved
0.6644	Remote Similarity	NPD5886	Approved
0.6643	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7240	Approved
0.6621	Remote Similarity	NPD6355	Discontinued
0.6618	Remote Similarity	NPD8379	Approved
0.6618	Remote Similarity	NPD8296	Approved
0.6618	Remote Similarity	NPD8378	Approved
0.6618	Remote Similarity	NPD8380	Approved
0.6618	Remote Similarity	NPD8335	Approved
0.6618	Remote Similarity	NPD7503	Approved
0.6614	Remote Similarity	NPD5909	Discontinued
0.66	Remote Similarity	NPD4628	Phase 3
0.6596	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD7199	Phase 2
0.6573	Remote Similarity	NPD3027	Phase 3
0.6571	Remote Similarity	NPD8651	Approved
0.6565	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD8294	Approved
0.6544	Remote Similarity	NPD8377	Approved
0.6541	Remote Similarity	NPD7058	Phase 2
0.6541	Remote Similarity	NPD7057	Phase 3
0.6533	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD969	Suspended
0.651	Remote Similarity	NPD6004	Phase 3
0.651	Remote Similarity	NPD6002	Phase 3
0.651	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.651	Remote Similarity	NPD6005	Phase 3
0.651	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD5124	Phase 1
0.6504	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6049	Phase 2
0.65	Remote Similarity	NPD5327	Phase 3
0.6496	Remote Similarity	NPD8033	Approved
0.649	Remote Similarity	NPD4110	Phase 3
0.649	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.649	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD2067	Discontinued
0.6486	Remote Similarity	NPD7305	Phase 1
0.6483	Remote Similarity	NPD6233	Phase 2
0.648	Remote Similarity	NPD4225	Approved
0.6471	Remote Similarity	NPD7610	Discontinued
0.6463	Remote Similarity	NPD6653	Approved
0.6463	Remote Similarity	NPD6353	Approved
0.6458	Remote Similarity	NPD7008	Discontinued
0.6454	Remote Similarity	NPD6696	Suspended
0.6446	Remote Similarity	NPD5844	Phase 1
0.6444	Remote Similarity	NPD7157	Approved
0.6438	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD1613	Approved
0.6434	Remote Similarity	NPD2861	Phase 2
0.6429	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.642	Remote Similarity	NPD8485	Approved
0.6415	Remote Similarity	NPD8455	Phase 2
0.6414	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD6798	Discontinued
0.6414	Remote Similarity	NPD7985	Registered
0.6414	Remote Similarity	NPD3764	Approved
0.6406	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD5058	Phase 3
0.6402	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4908	Phase 1
0.6387	Remote Similarity	NPD6273	Approved
0.6383	Remote Similarity	NPD7876	Discontinued
0.6382	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD7033	Discontinued
0.637	Remote Similarity	NPD7715	Approved
0.637	Remote Similarity	NPD8032	Phase 2
0.637	Remote Similarity	NPD4404	Approved
0.637	Remote Similarity	NPD5951	Approved
0.637	Remote Similarity	NPD7714	Approved
0.6364	Remote Similarity	NPD4624	Approved
0.6357	Remote Similarity	NPD4806	Approved
0.6357	Remote Similarity	NPD4807	Approved
0.635	Remote Similarity	NPD6065	Approved
0.6349	Remote Similarity	NPD5926	Approved
0.6341	Remote Similarity	NPD7229	Phase 3
0.6337	Remote Similarity	NPD8150	Discontinued
0.6336	Remote Similarity	NPD6686	Approved
0.6333	Remote Similarity	NPD7524	Approved
0.6333	Remote Similarity	NPD6100	Approved
0.6333	Remote Similarity	NPD6099	Approved
0.6331	Remote Similarity	NPD5305	Approved
0.6331	Remote Similarity	NPD5306	Approved
0.6331	Remote Similarity	NPD3019	Approved
0.6327	Remote Similarity	NPD2238	Phase 2
0.6324	Remote Similarity	NPD3317	Approved
0.6323	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1652	Phase 2
0.6316	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD7507	Approved
0.6312	Remote Similarity	NPD6637	Approved
0.6303	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD7319	Approved
0.629	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD2613	Approved
0.6275	Remote Similarity	NPD2575	Approved
0.6267	Remote Similarity	NPD5588	Approved
0.626	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD5691	Approved
0.6258	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6085	Phase 2
0.6243	Remote Similarity	NPD4663	Approved
0.6242	Remote Similarity	NPD3051	Approved
0.6242	Remote Similarity	NPD3787	Discontinued
0.6241	Remote Similarity	NPD3705	Approved
0.6233	Remote Similarity	NPD4625	Phase 3
0.6228	Remote Similarity	NPD7473	Discontinued
0.6225	Remote Similarity	NPD2438	Suspended
0.6222	Remote Similarity	NPD7635	Approved
0.6214	Remote Similarity	NPD4059	Approved
0.6214	Remote Similarity	NPD2932	Approved
0.6214	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD1778	Approved
0.6214	Remote Similarity	NPD4626	Approved
0.6214	Remote Similarity	NPD7725	Approved
0.6211	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5760	Phase 2
0.6211	Remote Similarity	NPD5761	Phase 2
0.621	Remote Similarity	NPD1088	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