NPASS Compound

Structure

NPC217447 OpenBabel07101719522D 27 29 0 0 0 0 0 0 0 0999 V2000 6.0622 -1.5000 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 -1.3660 0.3660 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 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 0.0000 -3.0000 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 -1.7321 -2.0000 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 0.0000 -2.0000 0.0000 C 0 0 0 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 -1.7321 -3.0000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 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 -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 -2.5981 -3.5000 0.0000 O 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 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 12 1 0 0 0 0 3 22 1 0 0 0 0 4 22 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 13 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 13 2 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 16 2 0 0 0 0 12 16 1 0 0 0 0 13 18 1 0 0 0 0 14 15 2 0 0 0 0 14 19 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 19 2 0 0 0 0 17 27 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 19 20 1 0 0 0 0 20 24 1 0 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.18
Volume:	388.895
LogP:	5.877
LogD:	3.508
LogS:	-3.156
# Rotatable Bonds:	5
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.635
Synthetic Accessibility Score:	2.856
Fsp3:	0.409
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.864
MDCK Permeability:	1.929737118189223e-05
Pgp-inhibitor:	0.172
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.306
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	100.3375473022461%
Volume Distribution (VD):	0.173
Pgp-substrate:	0.6135104894638062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.363
CYP1A2-substrate:	0.752
CYP2C19-inhibitor:	0.096
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.57
CYP2C9-substrate:	0.102
CYP2D6-inhibitor:	0.515
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.069
CYP3A4-substrate:	0.076

ADMET: Excretion

Clearance (CL):	1.089
Half-life (T1/2):	0.376

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.491
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.157
Maximum Recommended Daily Dose:	0.324
Skin Sensitization:	0.052
Carcinogencity:	0.138
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.888

Download Data

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

Natural Product: NPC217447

Natural Product ID:	NPC217447
*Common Name:**	8-Hydroxycannabinolic Acid A
IUPAC Name:	1,8-dihydroxy-6,6,9-trimethyl-3-pentylbenzo[c]chromene-2-carboxylic acid
Synonyms:
Standard InCHIKey:	DMVDJDMFQCOKJW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H26O5/c1-5-6-7-8-13-10-17-19(20(24)18(13)21(25)26)14-9-12(2)16(23)11-15(14)22(3,4)27-17/h9-11,23-24H,5-8H2,1-4H3,(H,25,26)
SMILES:	CCCCCc1cc2c(-c3cc(C)c(cc3C(C)(C)O2)O)c(c1C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL560418
PubChem CID:	44139742
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans

*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
IC50	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	3500.0	nM	PMID[481398]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	IC50	=	54000.0	nM	PMID[481398]
NPT19	Organism	Escherichia coli	Escherichia coli	IC50	=	54000.0	nM	PMID[481398]

☑ 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 NPC217447 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	381
0.1-0.2	1673
0.2-0.3	3777
0.3-0.4	8913
0.4-0.5	9514
0.5-0.6	3452
0.6-0.7	5289
0.7-0.8	6013
0.8-0.85	2473
0.85-0.9	1091
0.9-0.95	108
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9592	High Similarity	NPC150928
0.9589	High Similarity	NPC105415
0.9536	High Similarity	NPC474373
0.9524	High Similarity	NPC233267
0.9524	High Similarity	NPC291049
0.9463	High Similarity	NPC273483
0.9456	High Similarity	NPC37139
0.9404	High Similarity	NPC146211
0.9404	High Similarity	NPC4547
0.94	High Similarity	NPC472799
0.9396	High Similarity	NPC232645
0.9396	High Similarity	NPC133856
0.9396	High Similarity	NPC474417
0.9396	High Similarity	NPC149526
0.9396	High Similarity	NPC72958
0.9392	High Similarity	NPC97029
0.9392	High Similarity	NPC97028
0.9392	High Similarity	NPC158338
0.9392	High Similarity	NPC65589
0.9392	High Similarity	NPC288036
0.9392	High Similarity	NPC100985
0.9384	High Similarity	NPC32470
0.9333	High Similarity	NPC87708
0.9333	High Similarity	NPC175978
0.9329	High Similarity	NPC158866
0.9329	High Similarity	NPC325983
0.9324	High Similarity	NPC27221
0.9324	High Similarity	NPC7025
0.9324	High Similarity	NPC256672
0.932	High Similarity	NPC163846
0.932	High Similarity	NPC267509
0.932	High Similarity	NPC225173
0.9272	High Similarity	NPC329844
0.9272	High Similarity	NPC210942
0.9272	High Similarity	NPC169990
0.9267	High Similarity	NPC478148
0.9257	High Similarity	NPC125801
0.9257	High Similarity	NPC123202
0.9257	High Similarity	NPC22005
0.9257	High Similarity	NPC34802
0.9257	High Similarity	NPC7943
0.9252	High Similarity	NPC134621
0.9252	High Similarity	NPC29577
0.9211	High Similarity	NPC89625
0.9211	High Similarity	NPC149618
0.92	High Similarity	NPC202595
0.92	High Similarity	NPC119929
0.92	High Similarity	NPC227122
0.9189	High Similarity	NPC473927
0.9189	High Similarity	NPC237208
0.9184	High Similarity	NPC95123
0.9184	High Similarity	NPC66404
0.9178	High Similarity	NPC105648
0.9145	High Similarity	NPC280530
0.9145	High Similarity	NPC95842
0.9145	High Similarity	NPC477691
0.9145	High Similarity	NPC178964
0.9139	High Similarity	NPC258249
0.9133	High Similarity	NPC329933
0.9133	High Similarity	NPC70764
0.9133	High Similarity	NPC10027
0.9133	High Similarity	NPC65775
0.9128	High Similarity	NPC12305
0.9116	High Similarity	NPC84266
0.9116	High Similarity	NPC310340
0.911	High Similarity	NPC220106
0.911	High Similarity	NPC275734
0.9097	High Similarity	NPC143050
0.9091	High Similarity	NPC263483
0.9079	High Similarity	NPC477690
0.9079	High Similarity	NPC154683
0.9079	High Similarity	NPC40356
0.9079	High Similarity	NPC271681
0.9079	High Similarity	NPC142527
0.9073	High Similarity	NPC470107
0.9073	High Similarity	NPC307780
0.9073	High Similarity	NPC194379
0.9073	High Similarity	NPC309979
0.9067	High Similarity	NPC172329
0.9067	High Similarity	NPC2569
0.906	High Similarity	NPC290133
0.906	High Similarity	NPC196114
0.906	High Similarity	NPC24136
0.906	High Similarity	NPC473132
0.906	High Similarity	NPC473135
0.906	High Similarity	NPC187282
0.906	High Similarity	NPC470676
0.9054	High Similarity	NPC189650
0.9048	High Similarity	NPC182255
0.9048	High Similarity	NPC250755
0.9048	High Similarity	NPC94076
0.9041	High Similarity	NPC165172
0.9032	High Similarity	NPC177650
0.9032	High Similarity	NPC85121
0.9026	High Similarity	NPC180924
0.902	High Similarity	NPC135522
0.9013	High Similarity	NPC227166
0.9007	High Similarity	NPC269420
0.9007	High Similarity	NPC6923
0.9007	High Similarity	NPC473978
0.9	High Similarity	NPC477571
0.9	High Similarity	NPC140120
0.9	High Similarity	NPC477573
0.9	High Similarity	NPC477572
0.8994	High Similarity	NPC76647
0.8993	High Similarity	NPC470673
0.8993	High Similarity	NPC470674
0.8993	High Similarity	NPC131766
0.8993	High Similarity	NPC117716
0.8986	High Similarity	NPC144499
0.8986	High Similarity	NPC159721
0.8974	High Similarity	NPC470810
0.8974	High Similarity	NPC312993
0.8974	High Similarity	NPC119224
0.8974	High Similarity	NPC186325
0.8968	High Similarity	NPC201127
0.8968	High Similarity	NPC246647
0.8968	High Similarity	NPC272196
0.8968	High Similarity	NPC96342
0.8968	High Similarity	NPC268360
0.8968	High Similarity	NPC212967
0.8968	High Similarity	NPC164110
0.8961	High Similarity	NPC55662
0.8961	High Similarity	NPC166054
0.8961	High Similarity	NPC275575
0.8954	High Similarity	NPC45934
0.8947	High Similarity	NPC60413
0.8947	High Similarity	NPC472633
0.8947	High Similarity	NPC474660
0.8947	High Similarity	NPC295036
0.8947	High Similarity	NPC473466
0.894	High Similarity	NPC186397
0.894	High Similarity	NPC37135
0.8933	High Similarity	NPC477955
0.8933	High Similarity	NPC211565
0.8933	High Similarity	NPC260946
0.8933	High Similarity	NPC154217
0.8931	High Similarity	NPC125465
0.8931	High Similarity	NPC30027
0.8931	High Similarity	NPC178851
0.8926	High Similarity	NPC260152
0.8926	High Similarity	NPC18585
0.8926	High Similarity	NPC219915
0.8926	High Similarity	NPC166138
0.8926	High Similarity	NPC151607
0.8926	High Similarity	NPC42540
0.8926	High Similarity	NPC106985
0.8924	High Similarity	NPC207690
0.8924	High Similarity	NPC197168
0.8924	High Similarity	NPC156082
0.8924	High Similarity	NPC474350
0.8917	High Similarity	NPC273467
0.8917	High Similarity	NPC137232
0.8917	High Similarity	NPC66288
0.8917	High Similarity	NPC189552
0.8917	High Similarity	NPC18380
0.8912	High Similarity	NPC168471
0.8903	High Similarity	NPC474360
0.8903	High Similarity	NPC142339
0.8896	High Similarity	NPC324220
0.8896	High Similarity	NPC214632
0.8896	High Similarity	NPC235333
0.8896	High Similarity	NPC477669
0.8896	High Similarity	NPC312630
0.8889	High Similarity	NPC39819
0.8889	High Similarity	NPC305965
0.8882	High Similarity	NPC266499
0.8882	High Similarity	NPC237440
0.8882	High Similarity	NPC223988
0.8882	High Similarity	NPC298778
0.8882	High Similarity	NPC270160
0.8874	High Similarity	NPC56433
0.8874	High Similarity	NPC312929
0.8874	High Similarity	NPC259632
0.8874	High Similarity	NPC190648
0.8874	High Similarity	NPC289042
0.8874	High Similarity	NPC126767
0.8874	High Similarity	NPC308200
0.8874	High Similarity	NPC71055
0.8874	High Similarity	NPC118027
0.8874	High Similarity	NPC142863
0.8874	High Similarity	NPC245584
0.8868	High Similarity	NPC112981
0.8868	High Similarity	NPC25361
0.8867	High Similarity	NPC75694
0.8867	High Similarity	NPC271288
0.8867	High Similarity	NPC470890
0.8867	High Similarity	NPC1886
0.8867	High Similarity	NPC469953
0.8867	High Similarity	NPC312789
0.8867	High Similarity	NPC196137
0.8861	High Similarity	NPC473022
0.8861	High Similarity	NPC15374
0.8861	High Similarity	NPC470694
0.8859	High Similarity	NPC469542
0.8859	High Similarity	NPC51106
0.8859	High Similarity	NPC36181
0.8859	High Similarity	NPC471731
0.8859	High Similarity	NPC73028
0.8854	High Similarity	NPC292863

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 NPC217447 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	1001
0.2-0.3	1589
0.3-0.4	2563
0.4-0.5	1869
0.5-0.6	1110
0.6-0.7	442
0.7-0.8	172
0.8-0.85	43
0.85-0.9	12
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.902	High Similarity	NPD7819	Suspended
0.8917	High Similarity	NPD6959	Discontinued
0.8867	High Similarity	NPD2533	Approved
0.8867	High Similarity	NPD2532	Approved
0.8867	High Similarity	NPD2534	Approved
0.8861	High Similarity	NPD6232	Discontinued
0.8742	High Similarity	NPD4378	Clinical (unspecified phase)
0.8716	High Similarity	NPD970	Clinical (unspecified phase)
0.8696	High Similarity	NPD7473	Discontinued
0.8654	High Similarity	NPD2393	Clinical (unspecified phase)
0.8608	High Similarity	NPD3749	Approved
0.8589	High Similarity	NPD5844	Phase 1
0.8526	High Similarity	NPD7411	Suspended
0.8523	High Similarity	NPD2346	Discontinued
0.8516	High Similarity	NPD3226	Approved
0.8497	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD7075	Discontinued
0.8477	Intermediate Similarity	NPD3750	Approved
0.8477	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD7768	Phase 2
0.8418	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD1934	Approved
0.8344	Intermediate Similarity	NPD1549	Phase 2
0.8333	Intermediate Similarity	NPD6099	Approved
0.8333	Intermediate Similarity	NPD2935	Discontinued
0.8333	Intermediate Similarity	NPD6100	Approved
0.8312	Intermediate Similarity	NPD1511	Approved
0.8312	Intermediate Similarity	NPD7390	Discontinued
0.8302	Intermediate Similarity	NPD1465	Phase 2
0.8288	Intermediate Similarity	NPD4625	Phase 3
0.8282	Intermediate Similarity	NPD5711	Approved
0.8282	Intermediate Similarity	NPD5710	Approved
0.8267	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD1607	Approved
0.8228	Intermediate Similarity	NPD6599	Discontinued
0.8228	Intermediate Similarity	NPD4380	Phase 2
0.8214	Intermediate Similarity	NPD6559	Discontinued
0.8212	Intermediate Similarity	NPD1551	Phase 2
0.8205	Intermediate Similarity	NPD1512	Approved
0.8199	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD2801	Approved
0.817	Intermediate Similarity	NPD2800	Approved
0.817	Intermediate Similarity	NPD1243	Approved
0.8146	Intermediate Similarity	NPD3748	Approved
0.8146	Intermediate Similarity	NPD1510	Phase 2
0.8137	Intermediate Similarity	NPD3817	Phase 2
0.8125	Intermediate Similarity	NPD6801	Discontinued
0.8121	Intermediate Similarity	NPD1240	Approved
0.8092	Intermediate Similarity	NPD5404	Approved
0.8092	Intermediate Similarity	NPD5405	Approved
0.8092	Intermediate Similarity	NPD5408	Approved
0.8092	Intermediate Similarity	NPD5406	Approved
0.8092	Intermediate Similarity	NPD2796	Approved
0.8077	Intermediate Similarity	NPD6799	Approved
0.8052	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD2799	Discontinued
0.7987	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6166	Phase 2
0.7939	Intermediate Similarity	NPD5494	Approved
0.7929	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD920	Approved
0.7911	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD4628	Phase 3
0.7882	Intermediate Similarity	NPD7074	Phase 3
0.7867	Intermediate Similarity	NPD2313	Discontinued
0.7866	Intermediate Similarity	NPD3882	Suspended
0.7844	Intermediate Similarity	NPD7229	Phase 3
0.7824	Intermediate Similarity	NPD7054	Approved
0.7799	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD4308	Phase 3
0.7785	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7472	Approved
0.7771	Intermediate Similarity	NPD7003	Approved
0.777	Intermediate Similarity	NPD1203	Approved
0.7765	Intermediate Similarity	NPD3818	Discontinued
0.7755	Intermediate Similarity	NPD4749	Approved
0.7746	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5953	Discontinued
0.7733	Intermediate Similarity	NPD6797	Phase 2
0.7719	Intermediate Similarity	NPD7286	Phase 2
0.7703	Intermediate Similarity	NPD1283	Approved
0.7701	Intermediate Similarity	NPD8312	Approved
0.7701	Intermediate Similarity	NPD8313	Approved
0.7697	Intermediate Similarity	NPD5402	Approved
0.7692	Intermediate Similarity	NPD2344	Approved
0.7688	Intermediate Similarity	NPD7251	Discontinued
0.7687	Intermediate Similarity	NPD1608	Approved
0.7665	Intermediate Similarity	NPD919	Approved
0.7662	Intermediate Similarity	NPD6651	Approved
0.7661	Intermediate Similarity	NPD7177	Discontinued
0.7651	Intermediate Similarity	NPD2797	Approved
0.7644	Intermediate Similarity	NPD7808	Phase 3
0.7632	Intermediate Similarity	NPD411	Approved
0.7632	Intermediate Similarity	NPD3764	Approved
0.7632	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD3268	Approved
0.763	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD5403	Approved
0.759	Intermediate Similarity	NPD4288	Approved
0.7584	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4287	Approved
0.7576	Intermediate Similarity	NPD37	Approved
0.7568	Intermediate Similarity	NPD9717	Approved
0.7566	Intermediate Similarity	NPD7783	Phase 2
0.7566	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD7033	Discontinued
0.756	Intermediate Similarity	NPD6234	Discontinued
0.7553	Intermediate Similarity	NPD8151	Discontinued
0.7547	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD4965	Approved
0.7545	Intermediate Similarity	NPD4966	Approved
0.7545	Intermediate Similarity	NPD4967	Phase 2
0.7543	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2979	Phase 3
0.7532	Intermediate Similarity	NPD4307	Phase 2
0.7516	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD1201	Approved
0.75	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD422	Phase 1
0.75	Intermediate Similarity	NPD1281	Approved
0.75	Intermediate Similarity	NPD4908	Phase 1
0.7484	Intermediate Similarity	NPD5124	Phase 1
0.7484	Intermediate Similarity	NPD230	Phase 1
0.7484	Intermediate Similarity	NPD447	Suspended
0.7484	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4626	Approved
0.7483	Intermediate Similarity	NPD17	Approved
0.7473	Intermediate Similarity	NPD7435	Discontinued
0.7472	Intermediate Similarity	NPD8150	Discontinued
0.7471	Intermediate Similarity	NPD7199	Phase 2
0.7469	Intermediate Similarity	NPD5401	Approved
0.7457	Intermediate Similarity	NPD3751	Discontinued
0.7434	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD3787	Discontinued
0.7423	Intermediate Similarity	NPD6273	Approved
0.7419	Intermediate Similarity	NPD943	Approved
0.7419	Intermediate Similarity	NPD4060	Phase 1
0.7417	Intermediate Similarity	NPD1470	Approved
0.7417	Intermediate Similarity	NPD1164	Approved
0.7405	Intermediate Similarity	NPD6776	Approved
0.7405	Intermediate Similarity	NPD6782	Approved
0.7405	Intermediate Similarity	NPD6780	Approved
0.7405	Intermediate Similarity	NPD6781	Approved
0.7405	Intermediate Similarity	NPD6778	Approved
0.7405	Intermediate Similarity	NPD6777	Approved
0.7405	Intermediate Similarity	NPD6779	Approved
0.7394	Intermediate Similarity	NPD7458	Discontinued
0.7386	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD3926	Phase 2
0.7383	Intermediate Similarity	NPD1610	Phase 2
0.7383	Intermediate Similarity	NPD1611	Approved
0.7378	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2798	Approved
0.7368	Intermediate Similarity	NPD1247	Approved
0.7362	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7228	Approved
0.7351	Intermediate Similarity	NPD3225	Approved
0.7322	Intermediate Similarity	NPD4363	Phase 3
0.7322	Intermediate Similarity	NPD4360	Phase 2
0.7312	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3266	Approved
0.7303	Intermediate Similarity	NPD3267	Approved
0.7301	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5691	Approved
0.7297	Intermediate Similarity	NPD1651	Approved
0.7296	Intermediate Similarity	NPD4477	Approved
0.7296	Intermediate Similarity	NPD2438	Suspended
0.7296	Intermediate Similarity	NPD4476	Approved
0.7287	Intermediate Similarity	NPD7696	Phase 3
0.7287	Intermediate Similarity	NPD7698	Approved
0.7287	Intermediate Similarity	NPD7697	Approved
0.7278	Intermediate Similarity	NPD8434	Phase 2
0.7267	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1933	Approved
0.7257	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1471	Phase 3
0.725	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7870	Phase 2
0.7249	Intermediate Similarity	NPD7871	Phase 2
0.724	Intermediate Similarity	NPD7874	Approved
0.724	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6696	Suspended
0.7233	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8455	Phase 2
0.7209	Intermediate Similarity	NPD6746	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