NPASS Compound

Structure

NPC38604 OpenBabel07101719402D 24 26 0 0 1 0 0 0 0 0999 V2000 -4.3301 -1.5000 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 1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 1.3660 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 2.5981 -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 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 2.5981 0.5000 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 -0.8660 -2.5000 0.0000 C 0 0 0 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 3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 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 13 2 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 19 2 0 0 0 0 12 17 1 0 0 0 0 13 17 1 0 0 0 0 15 9 1 1 0 0 0 15 16 1 0 0 0 0 15 20 1 0 0 0 0 16 12 1 6 0 0 0 16 21 1 0 0 0 0 17 22 1 6 0 0 0 18 20 2 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.22
Volume:	361.928
LogP:	6.049
LogD:	4.54
LogS:	-2.741
# 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:	3.813
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:	-4.713
MDCK Permeability:	1.9049994079978205e-05
Pgp-inhibitor:	0.978
Pgp-substrate:	0.542
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.469
Plasma Protein Binding (PPB):	99.48201751708984%
Volume Distribution (VD):	3.191
Pgp-substrate:	1.9201017618179321%

ADMET: Metabolism

CYP1A2-inhibitor:	0.372
CYP1A2-substrate:	0.922
CYP2C19-inhibitor:	0.839
CYP2C19-substrate:	0.852
CYP2C9-inhibitor:	0.731
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.437
CYP2D6-substrate:	0.206
CYP3A4-inhibitor:	0.507
CYP3A4-substrate:	0.66

ADMET: Excretion

Clearance (CL):	5.384
Half-life (T1/2):	0.2

ADMET: Toxicity

hERG Blockers:	0.573
Human Hepatotoxicity (H-HT):	0.962
Drug-inuced Liver Injury (DILI):	0.22
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.63
Maximum Recommended Daily Dose:	0.982
Skin Sensitization:	0.095
Carcinogencity:	0.03
Eye Corrosion:	0.004
Eye Irritation:	0.045
Respiratory Toxicity:	0.914

Download Data

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

Natural Product: NPC38604

Natural Product ID:	NPC38604
*Common Name:**	8Alpha-Hydroxy-Delta9-Tetrahydrocannabinol
IUPAC Name:	(6aR,8S,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-1,8-diol
Synonyms:
Standard InCHIKey:	INKUWBOHCFHXTJ-ZACQAIPSSA-N
Standard InCHI:	InChI=1S/C21H30O3/c1-5-6-7-8-14-10-18(23)20-15-9-13(2)17(22)12-16(15)21(3,4)24-19(20)11-14/h9-11,15-17,22-23H,5-8,12H2,1-4H3/t15-,16-,17+/m1/s1
SMILES:	CCCCCc1cc(c2[C@@H]3C=C(C)[C@H](C[C@H]3C(C)(C)Oc2c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3586104
PubChem CID:	23620581
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	5

Activity Type	# Activity
Individual Protein	2
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	3219.0	nM	PMID[558263]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	1906.0	nM	PMID[558263]
NPT32	Organism	Mus musculus	Mus musculus	T	=	0.58	degrees C	PMID[558263]
NPT32	Organism	Mus musculus	Mus musculus	MPE	=	4.95	%	PMID[558263]
NPT32	Organism	Mus musculus	Mus musculus	MPE	=	5.01	%	PMID[558263]
NPT32	Organism	Mus musculus	Mus musculus	TIME	=	0.0004167	hr	PMID[558263]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	908.9	n.a.	PMID[558263]

☑ 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 NPC38604 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	NPC211179
0.9918	High Similarity	NPC472796
0.9918	High Similarity	NPC472795
0.9756	High Similarity	NPC472797
0.9587	High Similarity	NPC96940
0.9431	High Similarity	NPC476254
0.9431	High Similarity	NPC131397
0.937	High Similarity	NPC472798
0.9231	High Similarity	NPC472800
0.9187	High Similarity	NPC120638
0.9141	High Similarity	NPC472590
0.9106	High Similarity	NPC212965
0.9024	High Similarity	NPC218753
0.8984	High Similarity	NPC96719
0.8984	High Similarity	NPC222108
0.8939	High Similarity	NPC327735
0.8898	High Similarity	NPC50315
0.8898	High Similarity	NPC26879
0.8898	High Similarity	NPC230479
0.8898	High Similarity	NPC283049
0.888	High Similarity	NPC77789
0.888	High Similarity	NPC18128
0.8862	High Similarity	NPC85895
0.8862	High Similarity	NPC137294
0.8846	High Similarity	NPC160623
0.8837	High Similarity	NPC16577
0.8828	High Similarity	NPC46978
0.8819	High Similarity	NPC293801
0.881	High Similarity	NPC261992
0.8797	High Similarity	NPC126101
0.8779	High Similarity	NPC13005
0.8769	High Similarity	NPC27187
0.8769	High Similarity	NPC470225
0.876	High Similarity	NPC47283
0.876	High Similarity	NPC53986
0.876	High Similarity	NPC274717
0.876	High Similarity	NPC39064
0.876	High Similarity	NPC38664
0.874	High Similarity	NPC270030
0.8731	High Similarity	NPC134260
0.873	High Similarity	NPC36016
0.873	High Similarity	NPC188997
0.873	High Similarity	NPC100099
0.872	High Similarity	NPC96423
0.8712	High Similarity	NPC469610
0.871	High Similarity	NPC184302
0.871	High Similarity	NPC51341
0.8702	High Similarity	NPC181497
0.8702	High Similarity	NPC162801
0.8702	High Similarity	NPC271945
0.8702	High Similarity	NPC129106
0.8702	High Similarity	NPC150011
0.8702	High Similarity	NPC164574
0.8702	High Similarity	NPC268917
0.8702	High Similarity	NPC196765
0.8702	High Similarity	NPC280653
0.8702	High Similarity	NPC211413
0.8702	High Similarity	NPC164804
0.8702	High Similarity	NPC293203
0.8702	High Similarity	NPC207892
0.8702	High Similarity	NPC129784
0.8702	High Similarity	NPC17343
0.8702	High Similarity	NPC228369
0.8702	High Similarity	NPC300875
0.8702	High Similarity	NPC206224
0.8702	High Similarity	NPC244888
0.8702	High Similarity	NPC476166
0.8702	High Similarity	NPC118683
0.8702	High Similarity	NPC12875
0.8702	High Similarity	NPC236014
0.8702	High Similarity	NPC68205
0.8702	High Similarity	NPC118114
0.8692	High Similarity	NPC93962
0.8682	High Similarity	NPC473134
0.8678	High Similarity	NPC319803
0.8667	High Similarity	NPC471388
0.8661	High Similarity	NPC38761
0.8661	High Similarity	NPC76465
0.8657	High Similarity	NPC141717
0.8651	High Similarity	NPC54972
0.8651	High Similarity	NPC193364
0.8647	High Similarity	NPC115335
0.8647	High Similarity	NPC473107
0.8647	High Similarity	NPC198154
0.8647	High Similarity	NPC296915
0.8647	High Similarity	NPC223008
0.8647	High Similarity	NPC97834
0.8647	High Similarity	NPC225696
0.8636	High Similarity	NPC469611
0.8633	High Similarity	NPC471608
0.8629	High Similarity	NPC283616
0.8629	High Similarity	NPC190514
0.8615	High Similarity	NPC87224
0.8615	High Similarity	NPC222572
0.8605	High Similarity	NPC276212
0.8605	High Similarity	NPC471215
0.8605	High Similarity	NPC262573
0.8594	High Similarity	NPC246648
0.8594	High Similarity	NPC134195
0.8594	High Similarity	NPC86502
0.8594	High Similarity	NPC197351
0.8594	High Similarity	NPC106914
0.8583	High Similarity	NPC57199
0.8583	High Similarity	NPC74137
0.8582	High Similarity	NPC61946
0.8582	High Similarity	NPC151224
0.8582	High Similarity	NPC260898
0.8582	High Similarity	NPC47398
0.8582	High Similarity	NPC164787
0.8582	High Similarity	NPC234333
0.8571	High Similarity	NPC177712
0.8571	High Similarity	NPC85435
0.8571	High Similarity	NPC11060
0.8571	High Similarity	NPC24913
0.8571	High Similarity	NPC77196
0.8561	High Similarity	NPC472457
0.8561	High Similarity	NPC8899
0.8561	High Similarity	NPC103799
0.8561	High Similarity	NPC469557
0.8548	High Similarity	NPC69261
0.8548	High Similarity	NPC33270
0.854	High Similarity	NPC265075
0.854	High Similarity	NPC210192
0.854	High Similarity	NPC471389
0.8538	High Similarity	NPC149796
0.8529	High Similarity	NPC475836
0.8527	High Similarity	NPC470726
0.8527	High Similarity	NPC103420
0.8527	High Similarity	NPC17809
0.8527	High Similarity	NPC285040
0.8527	High Similarity	NPC188022
0.8527	High Similarity	NPC102540
0.8519	High Similarity	NPC16435
0.8519	High Similarity	NPC162659
0.8519	High Similarity	NPC269091
0.8519	High Similarity	NPC234952
0.8519	High Similarity	NPC306441
0.8519	High Similarity	NPC270456
0.8519	High Similarity	NPC470802
0.8519	High Similarity	NPC474639
0.8519	High Similarity	NPC230734
0.8519	High Similarity	NPC173660
0.8519	High Similarity	NPC248727
0.8519	High Similarity	NPC227503
0.8519	High Similarity	NPC265433
0.8519	High Similarity	NPC302701
0.8519	High Similarity	NPC476698
0.8507	High Similarity	NPC124085
0.8507	High Similarity	NPC117048
0.8492	Intermediate Similarity	NPC232295
0.8492	Intermediate Similarity	NPC258979
0.8492	Intermediate Similarity	NPC8283
0.8492	Intermediate Similarity	NPC93398
0.8492	Intermediate Similarity	NPC474131
0.8485	Intermediate Similarity	NPC262606
0.8485	Intermediate Similarity	NPC196193
0.8468	Intermediate Similarity	NPC150624
0.8467	Intermediate Similarity	NPC309124
0.8467	Intermediate Similarity	NPC184797
0.8467	Intermediate Similarity	NPC27495
0.8462	Intermediate Similarity	NPC82299
0.8456	Intermediate Similarity	NPC474687
0.845	Intermediate Similarity	NPC256015
0.845	Intermediate Similarity	NPC294156
0.8444	Intermediate Similarity	NPC112939
0.8444	Intermediate Similarity	NPC195022
0.8444	Intermediate Similarity	NPC94750
0.8444	Intermediate Similarity	NPC327382
0.8444	Intermediate Similarity	NPC473413
0.8444	Intermediate Similarity	NPC112246
0.8444	Intermediate Similarity	NPC121812
0.8444	Intermediate Similarity	NPC470356
0.8444	Intermediate Similarity	NPC474206
0.8443	Intermediate Similarity	NPC228452
0.844	Intermediate Similarity	NPC474397
0.8433	Intermediate Similarity	NPC92805
0.8433	Intermediate Similarity	NPC263064
0.843	Intermediate Similarity	NPC168657
0.8429	Intermediate Similarity	NPC90645
0.8425	Intermediate Similarity	NPC473875
0.8421	Intermediate Similarity	NPC268266
0.8421	Intermediate Similarity	NPC42760
0.8421	Intermediate Similarity	NPC268342
0.8421	Intermediate Similarity	NPC220825
0.8417	Intermediate Similarity	NPC477616
0.8413	Intermediate Similarity	NPC32152
0.8409	Intermediate Similarity	NPC134360
0.8406	Intermediate Similarity	NPC5155
0.8406	Intermediate Similarity	NPC247291
0.8406	Intermediate Similarity	NPC178054
0.84	Intermediate Similarity	NPC50521
0.84	Intermediate Similarity	NPC221549
0.84	Intermediate Similarity	NPC244816
0.8397	Intermediate Similarity	NPC66331
0.8397	Intermediate Similarity	NPC473221
0.8394	Intermediate Similarity	NPC25966
0.8394	Intermediate Similarity	NPC473739
0.8394	Intermediate Similarity	NPC70682
0.8394	Intermediate Similarity	NPC232164
0.8394	Intermediate Similarity	NPC236306

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 NPC38604 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
0.9587	High Similarity	NPD4749	Approved
0.952	High Similarity	NPD6410	Clinical (unspecified phase)
0.8837	High Similarity	NPD4625	Phase 3
0.875	High Similarity	NPD6917	Clinical (unspecified phase)
0.8651	High Similarity	NPD1610	Phase 2
0.8615	High Similarity	NPD4908	Phase 1
0.8485	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD6099	Approved
0.8456	Intermediate Similarity	NPD6100	Approved
0.8397	Intermediate Similarity	NPD2861	Phase 2
0.8358	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8358	Intermediate Similarity	NPD1613	Approved
0.8347	Intermediate Similarity	NPD4750	Phase 3
0.8345	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.824	Intermediate Similarity	NPD6671	Approved
0.8189	Intermediate Similarity	NPD1548	Phase 1
0.812	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.806	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD6696	Suspended
0.8	Intermediate Similarity	NPD3027	Phase 3
0.7899	Intermediate Similarity	NPD5124	Phase 1
0.7899	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD7340	Approved
0.7887	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD1091	Approved
0.7795	Intermediate Similarity	NPD1398	Phase 1
0.774	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD2238	Phase 2
0.7669	Intermediate Similarity	NPD422	Phase 1
0.76	Intermediate Similarity	NPD290	Approved
0.7586	Intermediate Similarity	NPD3892	Phase 2
0.7519	Intermediate Similarity	NPD1778	Approved
0.7517	Intermediate Similarity	NPD6674	Discontinued
0.75	Intermediate Similarity	NPD8651	Approved
0.7481	Intermediate Similarity	NPD2235	Phase 2
0.7481	Intermediate Similarity	NPD2231	Phase 2
0.7451	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7213	Phase 3
0.7432	Intermediate Similarity	NPD7212	Phase 2
0.7429	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD2200	Suspended
0.7402	Intermediate Similarity	NPD2684	Approved
0.7397	Intermediate Similarity	NPD1652	Phase 2
0.7394	Intermediate Similarity	NPD5735	Approved
0.7389	Intermediate Similarity	NPD6959	Discontinued
0.7386	Intermediate Similarity	NPD1934	Approved
0.7383	Intermediate Similarity	NPD7447	Phase 1
0.7381	Intermediate Similarity	NPD968	Approved
0.7379	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5763	Approved
0.7379	Intermediate Similarity	NPD5762	Approved
0.7361	Intermediate Similarity	NPD7033	Discontinued
0.7353	Intermediate Similarity	NPD2230	Approved
0.7353	Intermediate Similarity	NPD2233	Approved
0.7353	Intermediate Similarity	NPD2232	Approved
0.7351	Intermediate Similarity	NPD1653	Approved
0.7347	Intermediate Similarity	NPD7466	Approved
0.7339	Intermediate Similarity	NPD940	Approved
0.7339	Intermediate Similarity	NPD846	Approved
0.7333	Intermediate Similarity	NPD3496	Discontinued
0.7329	Intermediate Similarity	NPD1549	Phase 2
0.7324	Intermediate Similarity	NPD4060	Phase 1
0.7324	Intermediate Similarity	NPD4140	Approved
0.7319	Intermediate Similarity	NPD2797	Approved
0.7299	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD5327	Phase 3
0.7295	Intermediate Similarity	NPD288	Approved
0.729	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD7157	Approved
0.7267	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6584	Phase 3
0.726	Intermediate Similarity	NPD6002	Phase 3
0.726	Intermediate Similarity	NPD6004	Phase 3
0.726	Intermediate Similarity	NPD6005	Phase 3
0.726	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD4626	Approved
0.7244	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4967	Phase 2
0.7244	Intermediate Similarity	NPD4965	Approved
0.7244	Intermediate Similarity	NPD4966	Approved
0.723	Intermediate Similarity	NPD3750	Approved
0.7226	Intermediate Similarity	NPD1608	Approved
0.7222	Intermediate Similarity	NPD4097	Suspended
0.7222	Intermediate Similarity	NPD5844	Phase 1
0.7222	Intermediate Similarity	NPD6353	Approved
0.7214	Intermediate Similarity	NPD2237	Approved
0.7213	Intermediate Similarity	NPD844	Approved
0.7211	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD3620	Phase 2
0.7203	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1551	Phase 2
0.7192	Intermediate Similarity	NPD2796	Approved
0.719	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD5691	Approved
0.7176	Intermediate Similarity	NPD7843	Approved
0.7172	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4538	Approved
0.7172	Intermediate Similarity	NPD4536	Approved
0.7164	Intermediate Similarity	NPD7644	Approved
0.7162	Intermediate Similarity	NPD5177	Phase 3
0.7152	Intermediate Similarity	NPD2534	Approved
0.7152	Intermediate Similarity	NPD2532	Approved
0.7152	Intermediate Similarity	NPD2533	Approved
0.7152	Intermediate Similarity	NPD6234	Discontinued
0.7143	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6166	Phase 2
0.7143	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7819	Suspended
0.7103	Intermediate Similarity	NPD1607	Approved
0.7103	Intermediate Similarity	NPD6653	Approved
0.7095	Intermediate Similarity	NPD2424	Discontinued
0.7092	Intermediate Similarity	NPD3018	Phase 2
0.7092	Intermediate Similarity	NPD1712	Approved
0.7091	Intermediate Similarity	NPD6559	Discontinued
0.7089	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2677	Approved
0.7063	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3268	Approved
0.7063	Intermediate Similarity	NPD7985	Registered
0.7059	Intermediate Similarity	NPD5585	Approved
0.7055	Intermediate Similarity	NPD7228	Approved
0.705	Intermediate Similarity	NPD6582	Phase 2
0.705	Intermediate Similarity	NPD6583	Phase 3
0.7045	Intermediate Similarity	NPD7635	Approved
0.7042	Intermediate Similarity	NPD596	Approved
0.7042	Intermediate Similarity	NPD600	Approved
0.7029	Intermediate Similarity	NPD1611	Approved
0.7021	Intermediate Similarity	NPD3691	Phase 2
0.7021	Intermediate Similarity	NPD3690	Phase 2
0.7021	Intermediate Similarity	NPD4624	Approved
0.702	Intermediate Similarity	NPD5058	Phase 3
0.702	Intermediate Similarity	NPD3122	Phase 3
0.7007	Intermediate Similarity	NPD5588	Approved
0.7007	Intermediate Similarity	NPD17	Approved
0.7007	Intermediate Similarity	NPD5960	Phase 3
0.7007	Intermediate Similarity	NPD1510	Phase 2
0.7006	Intermediate Similarity	NPD2801	Approved
0.7	Intermediate Similarity	NPD6746	Phase 2
0.7	Intermediate Similarity	NPD4628	Phase 3
0.6993	Remote Similarity	NPD6090	Discontinued
0.6992	Remote Similarity	NPD5283	Phase 1
0.6985	Remote Similarity	NPD7741	Discontinued
0.6985	Remote Similarity	NPD3091	Approved
0.6984	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1242	Phase 1
0.6981	Remote Similarity	NPD7075	Discontinued
0.6974	Remote Similarity	NPD1511	Approved
0.697	Remote Similarity	NPD7074	Phase 3
0.697	Remote Similarity	NPD228	Approved
0.6966	Remote Similarity	NPD1240	Approved
0.6962	Remote Similarity	NPD5402	Approved
0.6957	Remote Similarity	NPD7199	Phase 2
0.695	Remote Similarity	NPD3094	Phase 2
0.6939	Remote Similarity	NPD7097	Phase 1
0.6934	Remote Similarity	NPD3443	Approved
0.6934	Remote Similarity	NPD3445	Approved
0.6934	Remote Similarity	NPD3444	Approved
0.6933	Remote Similarity	NPD2800	Approved
0.6929	Remote Similarity	NPD3685	Discontinued
0.6929	Remote Similarity	NPD2983	Phase 2
0.6929	Remote Similarity	NPD2982	Phase 2
0.6928	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6355	Discontinued
0.6918	Remote Similarity	NPD7768	Phase 2
0.6917	Remote Similarity	NPD821	Approved
0.6914	Remote Similarity	NPD7229	Phase 3
0.6914	Remote Similarity	NPD3787	Discontinued
0.6913	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7054	Approved
0.6908	Remote Similarity	NPD6667	Approved
0.6908	Remote Similarity	NPD6815	Approved
0.6908	Remote Similarity	NPD6666	Approved
0.6906	Remote Similarity	NPD3092	Approved
0.6906	Remote Similarity	NPD3705	Approved
0.6905	Remote Similarity	NPD3020	Approved
0.6901	Remote Similarity	NPD558	Phase 2
0.6899	Remote Similarity	NPD5929	Approved
0.6899	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD839	Approved
0.6897	Remote Similarity	NPD840	Approved
0.6894	Remote Similarity	NPD5494	Approved
0.6892	Remote Similarity	NPD4308	Phase 3
0.6892	Remote Similarity	NPD3748	Approved
0.6889	Remote Similarity	NPD2557	Approved
0.6887	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2667	Approved
0.6884	Remote Similarity	NPD2668	Approved
0.6884	Remote Similarity	NPD5846	Approved
0.6884	Remote Similarity	NPD5126	Approved
0.6884	Remote Similarity	NPD6516	Phase 2
0.6884	Remote Similarity	NPD5125	Phase 3
0.6883	Remote Similarity	NPD1512	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