NPASS Compound

Structure

NPC472796 OpenBabel07101718252D 24 26 0 0 1 0 0 0 0 0999 V2000 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 5 1 0 0 0 0 2 13 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 9 13 2 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 17 2 0 0 0 0 13 20 1 0 0 0 0 15 10 1 6 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 17 24 1 0 0 0 0 18 19 1 1 0 0 0 18 20 1 0 0 0 0 20 23 1 1 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.22
Volume:	361.928
LogP:	6.413
LogD:	4.687
LogS:	-2.69
# Rotatable Bonds:	4
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.621
Synthetic Accessibility Score:	3.827
Fsp3:	0.619
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.627
MDCK Permeability:	2.0882236640318297e-05
Pgp-inhibitor:	0.785
Pgp-substrate:	0.065
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.565
Plasma Protein Binding (PPB):	99.371337890625%
Volume Distribution (VD):	4.895
Pgp-substrate:	2.590424060821533%

ADMET: Metabolism

CYP1A2-inhibitor:	0.33
CYP1A2-substrate:	0.828
CYP2C19-inhibitor:	0.757
CYP2C19-substrate:	0.663
CYP2C9-inhibitor:	0.6
CYP2C9-substrate:	0.955
CYP2D6-inhibitor:	0.438
CYP2D6-substrate:	0.182
CYP3A4-inhibitor:	0.401
CYP3A4-substrate:	0.46

ADMET: Excretion

Clearance (CL):	6.97
Half-life (T1/2):	0.174

ADMET: Toxicity

hERG Blockers:	0.182
Human Hepatotoxicity (H-HT):	0.836
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.164
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.658
Carcinogencity:	0.067
Eye Corrosion:	0.007
Eye Irritation:	0.243
Respiratory Toxicity:	0.913

Download Data

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

Natural Product: NPC472796

Natural Product ID:	NPC472796
*Common Name:**	KQQMZTULVOWZJR-XFQXTVEOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KQQMZTULVOWZJR-XFQXTVEOSA-N
Standard InCHI:	InChI=1S/C21H30O3/c1-5-6-7-8-14-11-16(22)19-17(12-14)24-21(3,4)15-10-9-13(2)20(23)18(15)19/h9,11-12,15,18,20,22-23H,5-8,10H2,1-4H3/t15-,18-,20-/m1/s1
SMILES:	CCCCCC1=CC(=C2C3C(CC=C(C3O)C)C(OC2=C1)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3586107
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np50031a011]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18303850]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18681481]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19344127]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21902175]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26000707]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32880179]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7513	Cannabis sativa	Species	Cannabaceae	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
Ki	2
Others	10

Activity Type	# Activity
Individual Protein	2
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	3274.0	nM	PMID[566656]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	830.0	nM	PMID[566656]
NPT32	Organism	Mus musculus	Mus musculus	T	=	5.32	degrees C	PMID[566656]
NPT32	Organism	Mus musculus	Mus musculus	T	=	0.47	degrees C	PMID[566656]
NPT32	Organism	Mus musculus	Mus musculus	MPE	=	55.65	%	PMID[566656]
NPT32	Organism	Mus musculus	Mus musculus	MPE	=	6.819	%	PMID[566656]
NPT32	Organism	Mus musculus	Mus musculus	MPE	=	69.95	%	PMID[566656]
NPT32	Organism	Mus musculus	Mus musculus	MPE	=	2.2	%	PMID[566656]
NPT32	Organism	Mus musculus	Mus musculus	TIME	=	0.003806	hr	PMID[566656]
NPT32	Organism	Mus musculus	Mus musculus	TIME	=	0.0003889	hr	PMID[566656]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	2537.0	n.a.	PMID[566656]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	3045.0	n.a.	PMID[566656]

☑ 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 NPC472796 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	373
0.1-0.2	1472
0.2-0.3	4070
0.3-0.4	11205
0.4-0.5	7626
0.5-0.6	4528
0.6-0.7	8949
0.7-0.8	3844
0.8-0.85	488
0.85-0.9	124
0.9-0.95	9
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472795
0.9918	High Similarity	NPC211179
0.9918	High Similarity	NPC38604
0.9677	High Similarity	NPC472797
0.9508	High Similarity	NPC96940
0.9449	High Similarity	NPC472798
0.9355	High Similarity	NPC476254
0.9355	High Similarity	NPC131397
0.9308	High Similarity	NPC472800
0.9113	High Similarity	NPC120638
0.907	High Similarity	NPC472590
0.9062	High Similarity	NPC222108
0.9062	High Similarity	NPC96719
0.9032	High Similarity	NPC212965
0.9015	High Similarity	NPC327735
0.8952	High Similarity	NPC218753
0.8923	High Similarity	NPC160623
0.8915	High Similarity	NPC16577
0.8898	High Similarity	NPC293801
0.8872	High Similarity	NPC126101
0.8855	High Similarity	NPC13005
0.8846	High Similarity	NPC470225
0.8846	High Similarity	NPC27187
0.8837	High Similarity	NPC274717
0.8837	High Similarity	NPC53986
0.8837	High Similarity	NPC38664
0.8828	High Similarity	NPC230479
0.8828	High Similarity	NPC50315
0.8828	High Similarity	NPC283049
0.8828	High Similarity	NPC26879
0.881	High Similarity	NPC77789
0.881	High Similarity	NPC18128
0.879	High Similarity	NPC137294
0.879	High Similarity	NPC85895
0.8779	High Similarity	NPC244888
0.8779	High Similarity	NPC293203
0.8779	High Similarity	NPC207892
0.8779	High Similarity	NPC164804
0.8779	High Similarity	NPC300875
0.8779	High Similarity	NPC236014
0.8779	High Similarity	NPC129784
0.8779	High Similarity	NPC271945
0.8779	High Similarity	NPC206224
0.8779	High Similarity	NPC228369
0.8779	High Similarity	NPC68205
0.8779	High Similarity	NPC118114
0.8779	High Similarity	NPC476166
0.8779	High Similarity	NPC196765
0.8779	High Similarity	NPC118683
0.8779	High Similarity	NPC12875
0.8779	High Similarity	NPC17343
0.8779	High Similarity	NPC129106
0.8779	High Similarity	NPC181497
0.8779	High Similarity	NPC211413
0.8779	High Similarity	NPC268917
0.8779	High Similarity	NPC150011
0.8779	High Similarity	NPC164574
0.8779	High Similarity	NPC280653
0.8769	High Similarity	NPC93962
0.876	High Similarity	NPC473134
0.876	High Similarity	NPC46978
0.874	High Similarity	NPC261992
0.8722	High Similarity	NPC225696
0.8722	High Similarity	NPC473107
0.8722	High Similarity	NPC198154
0.8722	High Similarity	NPC296915
0.8722	High Similarity	NPC223008
0.8722	High Similarity	NPC97834
0.8722	High Similarity	NPC115335
0.8705	High Similarity	NPC471608
0.8692	High Similarity	NPC47283
0.8692	High Similarity	NPC39064
0.8682	High Similarity	NPC276212
0.8672	High Similarity	NPC134195
0.8672	High Similarity	NPC270030
0.8672	High Similarity	NPC197351
0.8672	High Similarity	NPC86502
0.8672	High Similarity	NPC246648
0.8672	High Similarity	NPC106914
0.8667	High Similarity	NPC134260
0.8661	High Similarity	NPC188997
0.8661	High Similarity	NPC57199
0.8661	High Similarity	NPC100099
0.8661	High Similarity	NPC36016
0.8651	High Similarity	NPC96423
0.8647	High Similarity	NPC85435
0.8647	High Similarity	NPC24913
0.8647	High Similarity	NPC469610
0.8647	High Similarity	NPC177712
0.8647	High Similarity	NPC77196
0.864	High Similarity	NPC184302
0.864	High Similarity	NPC51341
0.8636	High Similarity	NPC162801
0.8636	High Similarity	NPC103799
0.8633	High Similarity	NPC472457
0.8633	High Similarity	NPC469557
0.8615	High Similarity	NPC149796
0.8613	High Similarity	NPC265075
0.8607	High Similarity	NPC319803
0.8605	High Similarity	NPC102540
0.8605	High Similarity	NPC103420
0.8605	High Similarity	NPC285040
0.8605	High Similarity	NPC17809
0.8605	High Similarity	NPC470726
0.8605	High Similarity	NPC188022
0.8603	High Similarity	NPC475836
0.8603	High Similarity	NPC471388
0.8594	High Similarity	NPC76465
0.8594	High Similarity	NPC38761
0.8593	High Similarity	NPC470802
0.8593	High Similarity	NPC141717
0.8583	High Similarity	NPC193364
0.8583	High Similarity	NPC54972
0.8582	High Similarity	NPC117048
0.8582	High Similarity	NPC124085
0.8571	High Similarity	NPC232295
0.8571	High Similarity	NPC474131
0.8571	High Similarity	NPC469611
0.8561	High Similarity	NPC196193
0.856	High Similarity	NPC283616
0.856	High Similarity	NPC190514
0.855	High Similarity	NPC222572
0.855	High Similarity	NPC87224
0.8538	High Similarity	NPC262573
0.8538	High Similarity	NPC471215
0.8529	High Similarity	NPC474687
0.8519	High Similarity	NPC473413
0.8519	High Similarity	NPC47398
0.8519	High Similarity	NPC164787
0.8519	High Similarity	NPC234333
0.8519	High Similarity	NPC61946
0.8519	High Similarity	NPC151224
0.8519	High Similarity	NPC260898
0.8516	High Similarity	NPC74137
0.8511	High Similarity	NPC474397
0.8507	High Similarity	NPC92805
0.8507	High Similarity	NPC11060
0.85	High Similarity	NPC90645
0.8496	Intermediate Similarity	NPC8899
0.8492	Intermediate Similarity	NPC32152
0.8485	Intermediate Similarity	NPC134360
0.848	Intermediate Similarity	NPC69261
0.848	Intermediate Similarity	NPC33270
0.8478	Intermediate Similarity	NPC471389
0.8478	Intermediate Similarity	NPC210192
0.8478	Intermediate Similarity	NPC5155
0.8467	Intermediate Similarity	NPC32630
0.8467	Intermediate Similarity	NPC260741
0.8467	Intermediate Similarity	NPC70682
0.8462	Intermediate Similarity	NPC81641
0.8462	Intermediate Similarity	NPC158784
0.8462	Intermediate Similarity	NPC105031
0.8456	Intermediate Similarity	NPC474639
0.8456	Intermediate Similarity	NPC302701
0.8456	Intermediate Similarity	NPC230734
0.8456	Intermediate Similarity	NPC262585
0.8456	Intermediate Similarity	NPC20829
0.8456	Intermediate Similarity	NPC173660
0.8456	Intermediate Similarity	NPC306441
0.8456	Intermediate Similarity	NPC270456
0.8456	Intermediate Similarity	NPC265433
0.8456	Intermediate Similarity	NPC269091
0.8456	Intermediate Similarity	NPC18189
0.8456	Intermediate Similarity	NPC227503
0.8456	Intermediate Similarity	NPC248727
0.8456	Intermediate Similarity	NPC3049
0.8456	Intermediate Similarity	NPC16435
0.8456	Intermediate Similarity	NPC162659
0.8456	Intermediate Similarity	NPC234952
0.8456	Intermediate Similarity	NPC476698
0.8451	Intermediate Similarity	NPC212142
0.844	Intermediate Similarity	NPC233980
0.8438	Intermediate Similarity	NPC48623
0.8438	Intermediate Similarity	NPC168707
0.8429	Intermediate Similarity	NPC473845
0.8425	Intermediate Similarity	NPC282255
0.8425	Intermediate Similarity	NPC258979
0.8425	Intermediate Similarity	NPC8283
0.8425	Intermediate Similarity	NPC93398
0.8425	Intermediate Similarity	NPC3239
0.8421	Intermediate Similarity	NPC470727
0.8421	Intermediate Similarity	NPC262606
0.8417	Intermediate Similarity	NPC59841
0.8417	Intermediate Similarity	NPC475891
0.8417	Intermediate Similarity	NPC204347
0.8417	Intermediate Similarity	NPC2613
0.8406	Intermediate Similarity	NPC309124
0.8406	Intermediate Similarity	NPC259519
0.8406	Intermediate Similarity	NPC184797
0.8406	Intermediate Similarity	NPC27495
0.8403	Intermediate Similarity	NPC2745
0.8403	Intermediate Similarity	NPC302915
0.84	Intermediate Similarity	NPC150624
0.8397	Intermediate Similarity	NPC170485
0.8397	Intermediate Similarity	NPC470724
0.8397	Intermediate Similarity	NPC82299
0.8394	Intermediate Similarity	NPC477938
0.8385	Intermediate Similarity	NPC294156
0.8385	Intermediate Similarity	NPC256015
0.8382	Intermediate Similarity	NPC470356

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 NPC472796 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	921
0.2-0.3	1840
0.3-0.4	2737
0.4-0.5	1631
0.5-0.6	1026
0.6-0.7	576
0.7-0.8	79
0.8-0.85	12
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.96	High Similarity	NPD6410	Clinical (unspecified phase)
0.9508	High Similarity	NPD4749	Approved
0.8915	High Similarity	NPD4625	Phase 3
0.8828	High Similarity	NPD6917	Clinical (unspecified phase)
0.8583	High Similarity	NPD1610	Phase 2
0.8561	High Similarity	NPD4907	Clinical (unspecified phase)
0.855	High Similarity	NPD4908	Phase 1
0.8417	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD6099	Approved
0.8394	Intermediate Similarity	NPD6100	Approved
0.8333	Intermediate Similarity	NPD2861	Phase 2
0.8296	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8296	Intermediate Similarity	NPD1613	Approved
0.8279	Intermediate Similarity	NPD4750	Phase 3
0.8175	Intermediate Similarity	NPD6671	Approved
0.8125	Intermediate Similarity	NPD1548	Phase 1
0.8106	Intermediate Similarity	NPD6696	Suspended
0.806	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD5124	Phase 1
0.7971	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7969	Intermediate Similarity	NPD7340	Approved
0.7958	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD3027	Phase 3
0.7874	Intermediate Similarity	NPD1398	Phase 1
0.7744	Intermediate Similarity	NPD1091	Approved
0.7687	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2238	Phase 2
0.7612	Intermediate Similarity	NPD422	Phase 1
0.7586	Intermediate Similarity	NPD6674	Discontinued
0.7574	Intermediate Similarity	NPD8651	Approved
0.754	Intermediate Similarity	NPD290	Approved
0.7534	Intermediate Similarity	NPD3892	Phase 2
0.7516	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD5735	Approved
0.7463	Intermediate Similarity	NPD1778	Approved
0.7452	Intermediate Similarity	NPD6959	Discontinued
0.7448	Intermediate Similarity	NPD5762	Approved
0.7448	Intermediate Similarity	NPD5763	Approved
0.7426	Intermediate Similarity	NPD2235	Phase 2
0.7426	Intermediate Similarity	NPD2231	Phase 2
0.7394	Intermediate Similarity	NPD4060	Phase 1
0.7394	Intermediate Similarity	NPD4140	Approved
0.7383	Intermediate Similarity	NPD7212	Phase 2
0.7383	Intermediate Similarity	NPD7213	Phase 3
0.7383	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD5327	Phase 3
0.7372	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD2200	Suspended
0.7355	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1652	Phase 2
0.7344	Intermediate Similarity	NPD2684	Approved
0.7338	Intermediate Similarity	NPD37	Approved
0.7338	Intermediate Similarity	NPD1934	Approved
0.7333	Intermediate Similarity	NPD4626	Approved
0.7333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7447	Phase 1
0.7329	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6004	Phase 3
0.7329	Intermediate Similarity	NPD6002	Phase 3
0.7329	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6005	Phase 3
0.7323	Intermediate Similarity	NPD968	Approved
0.731	Intermediate Similarity	NPD7033	Discontinued
0.7308	Intermediate Similarity	NPD4967	Phase 2
0.7308	Intermediate Similarity	NPD4965	Approved
0.7308	Intermediate Similarity	NPD4966	Approved
0.7303	Intermediate Similarity	NPD1653	Approved
0.7299	Intermediate Similarity	NPD2230	Approved
0.7299	Intermediate Similarity	NPD2233	Approved
0.7299	Intermediate Similarity	NPD2232	Approved
0.7297	Intermediate Similarity	NPD7466	Approved
0.7292	Intermediate Similarity	NPD4097	Suspended
0.7292	Intermediate Similarity	NPD6353	Approved
0.7284	Intermediate Similarity	NPD5844	Phase 1
0.728	Intermediate Similarity	NPD846	Approved
0.728	Intermediate Similarity	NPD940	Approved
0.7279	Intermediate Similarity	NPD3496	Discontinued
0.7279	Intermediate Similarity	NPD1549	Phase 2
0.7273	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3620	Phase 2
0.7273	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD2797	Approved
0.7259	Intermediate Similarity	NPD5691	Approved
0.7255	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4536	Approved
0.7241	Intermediate Similarity	NPD4538	Approved
0.7241	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7644	Approved
0.7236	Intermediate Similarity	NPD288	Approved
0.7219	Intermediate Similarity	NPD2533	Approved
0.7219	Intermediate Similarity	NPD2532	Approved
0.7219	Intermediate Similarity	NPD2534	Approved
0.7218	Intermediate Similarity	NPD7157	Approved
0.7215	Intermediate Similarity	NPD6234	Discontinued
0.7214	Intermediate Similarity	NPD6584	Phase 3
0.7208	Intermediate Similarity	NPD4380	Phase 2
0.7197	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3750	Approved
0.7179	Intermediate Similarity	NPD7819	Suspended
0.7174	Intermediate Similarity	NPD1608	Approved
0.7163	Intermediate Similarity	NPD2237	Approved
0.7162	Intermediate Similarity	NPD2424	Discontinued
0.7162	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD844	Approved
0.7152	Intermediate Similarity	NPD6559	Discontinued
0.7143	Intermediate Similarity	NPD2796	Approved
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7133	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7985	Registered
0.7121	Intermediate Similarity	NPD7843	Approved
0.7121	Intermediate Similarity	NPD7635	Approved
0.7117	Intermediate Similarity	NPD7228	Approved
0.7114	Intermediate Similarity	NPD5177	Phase 3
0.7101	Intermediate Similarity	NPD1611	Approved
0.7099	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6166	Phase 2
0.7092	Intermediate Similarity	NPD4624	Approved
0.7092	Intermediate Similarity	NPD3691	Phase 2
0.7092	Intermediate Similarity	NPD3690	Phase 2
0.7086	Intermediate Similarity	NPD5058	Phase 3
0.7075	Intermediate Similarity	NPD5588	Approved
0.7075	Intermediate Similarity	NPD5960	Phase 3
0.7059	Intermediate Similarity	NPD7741	Discontinued
0.7059	Intermediate Similarity	NPD6090	Discontinued
0.7059	Intermediate Similarity	NPD3091	Approved
0.7055	Intermediate Similarity	NPD1607	Approved
0.7055	Intermediate Similarity	NPD6653	Approved
0.7044	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7075	Discontinued
0.7042	Intermediate Similarity	NPD1712	Approved
0.7042	Intermediate Similarity	NPD3018	Phase 2
0.7021	Intermediate Similarity	NPD3094	Phase 2
0.702	Intermediate Similarity	NPD2677	Approved
0.7014	Intermediate Similarity	NPD3268	Approved
0.7007	Intermediate Similarity	NPD5585	Approved
0.7007	Intermediate Similarity	NPD7097	Phase 1
0.7	Intermediate Similarity	NPD6583	Phase 3
0.7	Intermediate Similarity	NPD6582	Phase 2
0.7	Intermediate Similarity	NPD2800	Approved
0.6993	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD600	Approved
0.6993	Remote Similarity	NPD596	Approved
0.6981	Remote Similarity	NPD7768	Phase 2
0.6978	Remote Similarity	NPD3092	Approved
0.6975	Remote Similarity	NPD7229	Phase 3
0.6974	Remote Similarity	NPD6667	Approved
0.6974	Remote Similarity	NPD3122	Phase 3
0.6974	Remote Similarity	NPD6666	Approved
0.6962	Remote Similarity	NPD5929	Approved
0.6962	Remote Similarity	NPD2801	Approved
0.6962	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1510	Phase 2
0.6957	Remote Similarity	NPD6746	Phase 2
0.6957	Remote Similarity	NPD5126	Approved
0.6957	Remote Similarity	NPD5125	Phase 3
0.6957	Remote Similarity	NPD17	Approved
0.6957	Remote Similarity	NPD5494	Approved
0.6954	Remote Similarity	NPD4628	Phase 3
0.6954	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7411	Suspended
0.694	Remote Similarity	NPD5283	Phase 1
0.6939	Remote Similarity	NPD2157	Approved
0.6933	Remote Similarity	NPD2970	Approved
0.6933	Remote Similarity	NPD7037	Approved
0.6933	Remote Similarity	NPD2969	Approved
0.6929	Remote Similarity	NPD1242	Phase 1
0.6929	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7074	Phase 3
0.6928	Remote Similarity	NPD1511	Approved
0.6928	Remote Similarity	NPD7041	Phase 2
0.6928	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5402	Approved
0.6918	Remote Similarity	NPD1240	Approved
0.6917	Remote Similarity	NPD228	Approved
0.6914	Remote Similarity	NPD7199	Phase 2
0.6897	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.689	Remote Similarity	NPD27	Approved
0.689	Remote Similarity	NPD2489	Approved
0.6884	Remote Similarity	NPD3444	Approved
0.6884	Remote Similarity	NPD3445	Approved
0.6884	Remote Similarity	NPD3443	Approved
0.6879	Remote Similarity	NPD2983	Phase 2
0.6879	Remote Similarity	NPD2982	Phase 2
0.6879	Remote Similarity	NPD3685	Discontinued
0.6871	Remote Similarity	NPD6355	Discontinued
0.6871	Remote Similarity	NPD3787	Discontinued
0.6871	Remote Similarity	NPD6232	Discontinued
0.687	Remote Similarity	NPD2342	Discontinued
0.6867	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7054	Approved
0.6867	Remote Similarity	NPD7030	Discontinued
0.6867	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2346	Discontinued
0.6866	Remote Similarity	NPD821	Approved
0.6863	Remote Similarity	NPD6815	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