NPASS Compound

Structure

NPC182717 OpenBabel07101719522D 21 23 0 0 1 0 0 0 0 0999 V2000 4.6888 4.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2575 2.3912 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 3.7229 3.9659 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 1.7321 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 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 3.4641 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 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 6 19 1 0 0 0 0 7 8 1 0 0 0 0 7 14 2 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 15 20 1 1 0 0 0 16 18 1 0 0 0 0 16 20 1 1 0 0 0 17 18 1 0 0 0 0 17 21 1 1 0 0 0 19 4 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	332.324
LogP:	5.335
LogD:	4.685
LogS:	-4.829
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.665
Synthetic Accessibility Score:	4.434
Fsp3:	0.8
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:	-4.629
MDCK Permeability:	2.1071740775369108e-05
Pgp-inhibitor:	0.122
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.171
Plasma Protein Binding (PPB):	92.90995025634766%
Volume Distribution (VD):	1.122
Pgp-substrate:	6.651463508605957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.078
CYP1A2-substrate:	0.216
CYP2C19-inhibitor:	0.161
CYP2C19-substrate:	0.868
CYP2C9-inhibitor:	0.351
CYP2C9-substrate:	0.313
CYP2D6-inhibitor:	0.098
CYP2D6-substrate:	0.285
CYP3A4-inhibitor:	0.907
CYP3A4-substrate:	0.363

ADMET: Excretion

Clearance (CL):	4.752
Half-life (T1/2):	0.103

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.115
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.185
Maximum Recommended Daily Dose:	0.979
Skin Sensitization:	0.143
Carcinogencity:	0.073
Eye Corrosion:	0.058
Eye Irritation:	0.582
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC182717

Natural Product ID:	NPC182717
*Common Name:**	Isopimarane
IUPAC Name:	(2S,4aR,4bS,7S,10aR)-7-ethenyl-1,1,4a,7-tetramethyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthren-2-ol
Synonyms:	Isopimarane
Standard InCHIKey:	BLRQCWSOICYRPH-VDWQKOAOSA-N
Standard InCHI:	InChI=1S/C20H32O/c1-6-19(4)11-9-15-14(13-19)7-8-16-18(2,3)17(21)10-12-20(15,16)5/h6-7,15-17,21H,1,8-13H2,2-5H3/t15-,16-,17-,19-,20+/m0/s1
SMILES:	C=C[C@@]1(C)CC[C@H]2C(=CC[C@H]3C(C)(C)[C@H](CC[C@]23C)O)C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL225866
PubChem CID:	15541537
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO12671	Croton zambesicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17547457]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	feces	n.a.	n.a.	PMID[20402524]
NPO12671	Croton zambesicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12671	Croton zambesicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12671	Croton zambesicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO882	Trogopterus xanthipes	Species	Sciuridae	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	6
Others	1

Activity Type	# Activity
Cell Line	5
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	87800.0	nM	PMID[541893]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	40000.0	nM	PMID[541894]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[541894]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	40000.0	nM	PMID[541894]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	40000.0	nM	PMID[541894]
NPT177	Tissue	Aorta	Rattus norvegicus	IC50	=	46200.0	nM	PMID[541893]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	54.6	%	PMID[541893]

☑ 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 NPC182717 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	186
0.1-0.2	1487
0.2-0.3	6703
0.3-0.4	16479
0.4-0.5	7687
0.5-0.6	5415
0.6-0.7	3310
0.7-0.8	1087
0.8-0.85	196
0.85-0.9	106
0.9-0.95	34
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC477138
0.9565	High Similarity	NPC91858
0.9565	High Similarity	NPC100334
0.9565	High Similarity	NPC243342
0.9559	High Similarity	NPC110799
0.9437	High Similarity	NPC471798
0.9429	High Similarity	NPC291503
0.942	High Similarity	NPC471799
0.9412	High Similarity	NPC145498
0.9296	High Similarity	NPC290598
0.9296	High Similarity	NPC129165
0.9296	High Similarity	NPC265328
0.9296	High Similarity	NPC134330
0.9296	High Similarity	NPC30590
0.9296	High Similarity	NPC122418
0.9296	High Similarity	NPC27765
0.9296	High Similarity	NPC189883
0.9296	High Similarity	NPC106432
0.9296	High Similarity	NPC120098
0.9286	High Similarity	NPC471797
0.9275	High Similarity	NPC167706
0.9275	High Similarity	NPC242001
0.9254	High Similarity	NPC197805
0.9167	High Similarity	NPC472805
0.9167	High Similarity	NPC101475
0.9167	High Similarity	NPC91594
0.9167	High Similarity	NPC40394
0.9167	High Similarity	NPC34177
0.9167	High Similarity	NPC157996
0.9167	High Similarity	NPC90979
0.9155	High Similarity	NPC34700
0.9155	High Similarity	NPC141071
0.9155	High Similarity	NPC471723
0.9155	High Similarity	NPC257347
0.9155	High Similarity	NPC138374
0.9155	High Similarity	NPC477923
0.9155	High Similarity	NPC66566
0.9118	High Similarity	NPC208999
0.9104	High Similarity	NPC476039
0.9104	High Similarity	NPC286669
0.9104	High Similarity	NPC222366
0.9041	High Similarity	NPC470396
0.9041	High Similarity	NPC99168
0.9041	High Similarity	NPC253807
0.9041	High Similarity	NPC474989
0.9041	High Similarity	NPC98386
0.9041	High Similarity	NPC22955
0.9041	High Similarity	NPC300499
0.9041	High Similarity	NPC158662
0.9041	High Similarity	NPC196753
0.9041	High Similarity	NPC230295
0.9028	High Similarity	NPC113733
0.9028	High Similarity	NPC265588
0.9028	High Similarity	NPC237460
0.9028	High Similarity	NPC46160
0.9028	High Similarity	NPC240604
0.9028	High Similarity	NPC106364
0.9028	High Similarity	NPC470362
0.9028	High Similarity	NPC300324
0.9028	High Similarity	NPC202642
0.8933	High Similarity	NPC476646
0.8919	High Similarity	NPC53744
0.8919	High Similarity	NPC1319
0.8919	High Similarity	NPC291379
0.8904	High Similarity	NPC470711
0.8904	High Similarity	NPC477924
0.8904	High Similarity	NPC470758
0.8904	High Similarity	NPC214570
0.8904	High Similarity	NPC130136
0.8889	High Similarity	NPC304309
0.8889	High Similarity	NPC285893
0.8889	High Similarity	NPC118508
0.8889	High Similarity	NPC134847
0.8889	High Similarity	NPC162742
0.8889	High Similarity	NPC121744
0.8889	High Similarity	NPC28657
0.8889	High Similarity	NPC230301
0.8889	High Similarity	NPC22105
0.8889	High Similarity	NPC136188
0.8889	High Similarity	NPC288035
0.8889	High Similarity	NPC322353
0.8873	High Similarity	NPC68443
0.8857	High Similarity	NPC92801
0.8841	High Similarity	NPC94192
0.8841	High Similarity	NPC32055
0.8806	High Similarity	NPC225415
0.88	High Similarity	NPC96362
0.88	High Similarity	NPC287749
0.88	High Similarity	NPC295131
0.88	High Similarity	NPC236112
0.8784	High Similarity	NPC11908
0.8784	High Similarity	NPC83351
0.8784	High Similarity	NPC244385
0.8784	High Similarity	NPC76931
0.8784	High Similarity	NPC275910
0.8784	High Similarity	NPC167891
0.8784	High Similarity	NPC85346
0.8784	High Similarity	NPC65897
0.8784	High Similarity	NPC138621
0.8784	High Similarity	NPC186191
0.8784	High Similarity	NPC318136
0.8784	High Similarity	NPC302041
0.8784	High Similarity	NPC72507
0.8784	High Similarity	NPC312328
0.8784	High Similarity	NPC6978
0.8784	High Similarity	NPC205455
0.8784	High Similarity	NPC307965
0.8784	High Similarity	NPC285761
0.8784	High Similarity	NPC18603
0.8784	High Similarity	NPC167037
0.8767	High Similarity	NPC321016
0.8767	High Similarity	NPC321381
0.8767	High Similarity	NPC107059
0.8767	High Similarity	NPC470749
0.8767	High Similarity	NPC274079
0.8767	High Similarity	NPC477925
0.8767	High Similarity	NPC253190
0.8767	High Similarity	NPC73875
0.875	High Similarity	NPC469534
0.875	High Similarity	NPC201048
0.875	High Similarity	NPC476366
0.875	High Similarity	NPC469533
0.875	High Similarity	NPC469593
0.8732	High Similarity	NPC164022
0.8714	High Similarity	NPC210323
0.8714	High Similarity	NPC476431
0.8701	High Similarity	NPC237795
0.8701	High Similarity	NPC82538
0.8684	High Similarity	NPC142163
0.8684	High Similarity	NPC249423
0.8684	High Similarity	NPC474531
0.8684	High Similarity	NPC242350
0.8676	High Similarity	NPC163678
0.8667	High Similarity	NPC30986
0.8667	High Similarity	NPC80530
0.8667	High Similarity	NPC472463
0.8667	High Similarity	NPC273410
0.8667	High Similarity	NPC209430
0.8649	High Similarity	NPC34019
0.8649	High Similarity	NPC155986
0.8649	High Similarity	NPC198968
0.8649	High Similarity	NPC318495
0.8611	High Similarity	NPC201373
0.8592	High Similarity	NPC45296
0.8592	High Similarity	NPC34834
0.859	High Similarity	NPC470077
0.8571	High Similarity	NPC30166
0.8571	High Similarity	NPC87489
0.8571	High Similarity	NPC248886
0.8571	High Similarity	NPC216460
0.8571	High Similarity	NPC96484
0.8571	High Similarity	NPC296701
0.8571	High Similarity	NPC49964
0.8571	High Similarity	NPC218616
0.8571	High Similarity	NPC47763
0.8571	High Similarity	NPC304285
0.8571	High Similarity	NPC2648
0.8571	High Similarity	NPC470049
0.8553	High Similarity	NPC234193
0.8553	High Similarity	NPC102253
0.8553	High Similarity	NPC164840
0.8553	High Similarity	NPC236237
0.8553	High Similarity	NPC241290
0.8553	High Similarity	NPC209944
0.8553	High Similarity	NPC322313
0.8553	High Similarity	NPC13554
0.8551	High Similarity	NPC149680
0.8533	High Similarity	NPC477522
0.8533	High Similarity	NPC473943
0.8533	High Similarity	NPC474216
0.8533	High Similarity	NPC476314
0.8533	High Similarity	NPC87604
0.8533	High Similarity	NPC148977
0.8529	High Similarity	NPC290367
0.8514	High Similarity	NPC247325
0.8514	High Similarity	NPC96319
0.8514	High Similarity	NPC244488
0.8493	Intermediate Similarity	NPC306727
0.8481	Intermediate Similarity	NPC318390
0.8472	Intermediate Similarity	NPC301226
0.8472	Intermediate Similarity	NPC111234
0.8462	Intermediate Similarity	NPC159168
0.8462	Intermediate Similarity	NPC52108
0.8462	Intermediate Similarity	NPC474789
0.8462	Intermediate Similarity	NPC253402
0.8462	Intermediate Similarity	NPC477818
0.8451	Intermediate Similarity	NPC9942
0.8442	Intermediate Similarity	NPC264245
0.8442	Intermediate Similarity	NPC47761
0.8442	Intermediate Similarity	NPC116202
0.8442	Intermediate Similarity	NPC470383
0.8421	Intermediate Similarity	NPC328714
0.8421	Intermediate Similarity	NPC109546
0.8421	Intermediate Similarity	NPC81306
0.8421	Intermediate Similarity	NPC100906
0.8421	Intermediate Similarity	NPC143182
0.8421	Intermediate Similarity	NPC28862
0.8421	Intermediate Similarity	NPC47982
0.8421	Intermediate Similarity	NPC84694
0.8406	Intermediate Similarity	NPC64123

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 NPC182717 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1760
0.2-0.3	4177
0.3-0.4	2137
0.4-0.5	499
0.5-0.6	179
0.6-0.7	163
0.7-0.8	44
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8919	High Similarity	NPD7645	Phase 2
0.8889	High Similarity	NPD7339	Approved
0.8889	High Similarity	NPD6942	Approved
0.8553	High Similarity	NPD7525	Registered
0.8514	High Similarity	NPD3701	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4784	Approved
0.8	Intermediate Similarity	NPD4785	Approved
0.7973	Intermediate Similarity	NPD7151	Approved
0.7973	Intermediate Similarity	NPD7152	Approved
0.7973	Intermediate Similarity	NPD7150	Approved
0.7973	Intermediate Similarity	NPD4243	Approved
0.7927	Intermediate Similarity	NPD3618	Phase 1
0.7901	Intermediate Similarity	NPD4786	Approved
0.7895	Intermediate Similarity	NPD8264	Approved
0.7882	Intermediate Similarity	NPD6079	Approved
0.7875	Intermediate Similarity	NPD3667	Approved
0.7857	Intermediate Similarity	NPD5328	Approved
0.7838	Intermediate Similarity	NPD7144	Approved
0.7838	Intermediate Similarity	NPD7143	Approved
0.7763	Intermediate Similarity	NPD6924	Approved
0.7763	Intermediate Similarity	NPD6926	Approved
0.7703	Intermediate Similarity	NPD6923	Approved
0.7703	Intermediate Similarity	NPD6922	Approved
0.7674	Intermediate Similarity	NPD7515	Phase 2
0.7564	Intermediate Similarity	NPD6933	Approved
0.747	Intermediate Similarity	NPD3665	Phase 1
0.747	Intermediate Similarity	NPD3666	Approved
0.747	Intermediate Similarity	NPD3133	Approved
0.7436	Intermediate Similarity	NPD4190	Phase 3
0.7436	Intermediate Similarity	NPD5275	Approved
0.7412	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4748	Discontinued
0.7407	Intermediate Similarity	NPD7509	Discontinued
0.7386	Intermediate Similarity	NPD4202	Approved
0.7333	Intermediate Similarity	NPD5221	Approved
0.7333	Intermediate Similarity	NPD5222	Approved
0.7333	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7748	Approved
0.7284	Intermediate Similarity	NPD6929	Approved
0.7284	Intermediate Similarity	NPD4195	Approved
0.7253	Intermediate Similarity	NPD5173	Approved
0.725	Intermediate Similarity	NPD6932	Approved
0.7195	Intermediate Similarity	NPD6931	Approved
0.7195	Intermediate Similarity	NPD6930	Phase 2
0.7176	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5290	Discontinued
0.716	Intermediate Similarity	NPD7145	Approved
0.716	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4697	Phase 3
0.7097	Intermediate Similarity	NPD4696	Approved
0.7097	Intermediate Similarity	NPD5286	Approved
0.7097	Intermediate Similarity	NPD5285	Approved
0.7065	Intermediate Similarity	NPD4755	Approved
0.7065	Intermediate Similarity	NPD7902	Approved
0.7059	Intermediate Similarity	NPD3668	Phase 3
0.7037	Intermediate Similarity	NPD6925	Approved
0.7037	Intermediate Similarity	NPD5776	Phase 2
0.7021	Intermediate Similarity	NPD5223	Approved
0.7	Intermediate Similarity	NPD6399	Phase 3
0.6989	Remote Similarity	NPD7638	Approved
0.6988	Remote Similarity	NPD7332	Phase 2
0.6988	Remote Similarity	NPD7514	Phase 3
0.6986	Remote Similarity	NPD368	Approved
0.6947	Remote Similarity	NPD5225	Approved
0.6947	Remote Similarity	NPD5226	Approved
0.6947	Remote Similarity	NPD5224	Approved
0.6947	Remote Similarity	NPD4633	Approved
0.6947	Remote Similarity	NPD5211	Phase 2
0.6941	Remote Similarity	NPD6695	Phase 3
0.6915	Remote Similarity	NPD7640	Approved
0.6915	Remote Similarity	NPD4700	Approved
0.6915	Remote Similarity	NPD7639	Approved
0.6905	Remote Similarity	NPD6902	Approved
0.6897	Remote Similarity	NPD5279	Phase 3
0.6875	Remote Similarity	NPD5175	Approved
0.6875	Remote Similarity	NPD5174	Approved
0.6867	Remote Similarity	NPD6683	Phase 2
0.686	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD342	Phase 1
0.6854	Remote Similarity	NPD4753	Phase 2
0.6824	Remote Similarity	NPD4221	Approved
0.6824	Remote Similarity	NPD4223	Phase 3
0.6804	Remote Similarity	NPD5141	Approved
0.6795	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4695	Discontinued
0.6782	Remote Similarity	NPD5329	Approved
0.6782	Remote Similarity	NPD6893	Approved
0.6768	Remote Similarity	NPD6899	Approved
0.6768	Remote Similarity	NPD6881	Approved
0.6739	Remote Similarity	NPD7900	Approved
0.6739	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6402	Approved
0.6735	Remote Similarity	NPD7128	Approved
0.6735	Remote Similarity	NPD6675	Approved
0.6735	Remote Similarity	NPD5739	Approved
0.6706	Remote Similarity	NPD6898	Phase 1
0.6705	Remote Similarity	NPD4623	Approved
0.6705	Remote Similarity	NPD4519	Discontinued
0.6705	Remote Similarity	NPD6684	Approved
0.6705	Remote Similarity	NPD7521	Approved
0.6705	Remote Similarity	NPD7334	Approved
0.6705	Remote Similarity	NPD6409	Approved
0.6705	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7146	Approved
0.6705	Remote Similarity	NPD5330	Approved
0.6703	Remote Similarity	NPD6411	Approved
0.6701	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6634	Remote Similarity	NPD7102	Approved
0.6634	Remote Similarity	NPD7290	Approved
0.6634	Remote Similarity	NPD6883	Approved
0.6629	Remote Similarity	NPD7750	Discontinued
0.6629	Remote Similarity	NPD3573	Approved
0.6629	Remote Similarity	NPD7524	Approved
0.66	Remote Similarity	NPD4729	Approved
0.66	Remote Similarity	NPD6011	Approved
0.66	Remote Similarity	NPD4730	Approved
0.66	Remote Similarity	NPD5168	Approved
0.66	Remote Similarity	NPD7320	Approved
0.6588	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6650	Approved
0.6569	Remote Similarity	NPD6847	Approved
0.6569	Remote Similarity	NPD6869	Approved
0.6569	Remote Similarity	NPD6649	Approved
0.6569	Remote Similarity	NPD6617	Approved
0.6569	Remote Similarity	NPD8130	Phase 1
0.6566	Remote Similarity	NPD4768	Approved
0.6566	Remote Similarity	NPD4767	Approved
0.6556	Remote Similarity	NPD6903	Approved
0.6556	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4788	Approved
0.6548	Remote Similarity	NPD3617	Approved
0.6535	Remote Similarity	NPD6012	Approved
0.6535	Remote Similarity	NPD6373	Approved
0.6535	Remote Similarity	NPD6014	Approved
0.6535	Remote Similarity	NPD6013	Approved
0.6535	Remote Similarity	NPD6372	Approved
0.6528	Remote Similarity	NPD4219	Approved
0.6526	Remote Similarity	NPD6083	Phase 2
0.6526	Remote Similarity	NPD6084	Phase 2
0.6522	Remote Similarity	NPD8035	Phase 2
0.6522	Remote Similarity	NPD8034	Phase 2
0.6517	Remote Similarity	NPD5690	Phase 2
0.6517	Remote Similarity	NPD4688	Approved
0.6517	Remote Similarity	NPD4689	Approved
0.6517	Remote Similarity	NPD5205	Approved
0.6517	Remote Similarity	NPD4690	Approved
0.6517	Remote Similarity	NPD4138	Approved
0.6517	Remote Similarity	NPD4693	Phase 3
0.6505	Remote Similarity	NPD8297	Approved
0.6505	Remote Similarity	NPD6882	Approved
0.65	Remote Similarity	NPD5701	Approved
0.65	Remote Similarity	NPD4787	Phase 1
0.6484	Remote Similarity	NPD6101	Approved
0.6484	Remote Similarity	NPD6051	Approved
0.6484	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5169	Approved
0.6471	Remote Similarity	NPD5247	Approved
0.6471	Remote Similarity	NPD5248	Approved
0.6471	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4634	Approved
0.6471	Remote Similarity	NPD5249	Phase 3
0.6471	Remote Similarity	NPD5251	Approved
0.6471	Remote Similarity	NPD5135	Approved
0.6471	Remote Similarity	NPD5250	Approved
0.6458	Remote Similarity	NPD4225	Approved
0.6436	Remote Similarity	NPD5128	Approved
0.642	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.642	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD384	Approved
0.6418	Remote Similarity	NPD385	Approved
0.6408	Remote Similarity	NPD5217	Approved
0.6408	Remote Similarity	NPD5215	Approved
0.6408	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5127	Approved
0.6408	Remote Similarity	NPD5216	Approved
0.6375	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6672	Approved
0.6374	Remote Similarity	NPD4722	Approved
0.6374	Remote Similarity	NPD5737	Approved
0.6374	Remote Similarity	NPD4723	Approved
0.6344	Remote Similarity	NPD7087	Discontinued
0.6333	Remote Similarity	NPD4694	Approved
0.6333	Remote Similarity	NPD5280	Approved
0.6327	Remote Similarity	NPD4159	Approved
0.6321	Remote Similarity	NPD6868	Approved
0.631	Remote Similarity	NPD6117	Approved
0.6304	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4632	Approved
0.6265	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7632	Discontinued
0.6262	Remote Similarity	NPD7115	Discovery
0.625	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD7136	Phase 2
0.6235	Remote Similarity	NPD6116	Phase 1
0.6226	Remote Similarity	NPD5167	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