NPASS Compound

Structure

CID110799 OpenBabel06191715462D 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 0 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 1 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 2 0 0 0 0 15 20 1 0 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:	4.809
LogD:	4.11
LogS:	-2.908
# 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:	0.653
Synthetic Accessibility Score:	4.365
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:	-4.772
MDCK Permeability:	1.7047823348548263e-05
Pgp-inhibitor:	0.643
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.875
30% Bioavailability (F30%):	0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.127
Plasma Protein Binding (PPB):	92.3133316040039%
Volume Distribution (VD):	1.318
Pgp-substrate:	5.005903244018555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.294
CYP2C19-inhibitor:	0.141
CYP2C19-substrate:	0.92
CYP2C9-inhibitor:	0.264
CYP2C9-substrate:	0.259
CYP2D6-inhibitor:	0.083
CYP2D6-substrate:	0.185
CYP3A4-inhibitor:	0.9
CYP3A4-substrate:	0.596

ADMET: Excretion

Clearance (CL):	12.495
Half-life (T1/2):	0.082

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.174
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.489
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.22
Carcinogencity:	0.242
Eye Corrosion:	0.091
Eye Irritation:	0.127
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC110799

Natural Product ID:	NPC110799
*Common Name:**	1Isopimara-8,15-Dien-3Beta-Ol
IUPAC Name:	(2S,4aS,7S,10aR)-7-ethenyl-1,1,4a,7-tetramethyl-3,4,5,6,8,9,10,10a-octahydro-2H-phenanthren-2-ol
Synonyms:
Standard InCHIKey:	UPEXJUYHODZFMO-QGZVKYPTSA-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/h6,16-17,21H,1,7-13H2,2-5H3/t16-,17-,19-,20+/m0/s1
SMILES:	C=C[C@@]1(C)CCC2=C(C1)CC[C@@H]1[C@]2(C)CC[C@@H](C1(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL254635
PubChem CID:	10108199
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
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	Leaves and branches	Soorkesh Valley, Gollestan, Iran	n.a.	PMID[15104493]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	leaves	Soorkesh Valley, Gollestan, Iran	n.a.	PMID[15104493]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	feces	n.a.	n.a.	PMID[20402524]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28256	Platycladus orientalis	Species	Cupressaceae	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

Activity Type	# Activity
Cell Line	4
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	40000.0	nM	PMID[447759]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[447759]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	40000.0	nM	PMID[447759]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	40000.0	nM	PMID[447759]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	7.0	ug.mL-1	PMID[447757]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	24600.0	nM	PMID[447758]

☑ 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 NPC110799 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	180
0.1-0.2	1574
0.2-0.3	7731
0.3-0.4	16577
0.4-0.5	7741
0.5-0.6	5586
0.6-0.7	2513
0.7-0.8	655
0.8-0.85	93
0.85-0.9	39
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9559	High Similarity	NPC182717
0.9155	High Similarity	NPC46160
0.9155	High Similarity	NPC202642
0.9155	High Similarity	NPC470362
0.9155	High Similarity	NPC106432
0.9143	High Similarity	NPC243342
0.9143	High Similarity	NPC100334
0.9143	High Similarity	NPC91858
0.9143	High Similarity	NPC477138
0.9091	High Similarity	NPC163678
0.9028	High Similarity	NPC471798
0.9028	High Similarity	NPC214570
0.9014	High Similarity	NPC291503
0.9014	High Similarity	NPC118508
0.9014	High Similarity	NPC322353
0.9014	High Similarity	NPC121744
0.9014	High Similarity	NPC138374
0.9014	High Similarity	NPC34700
0.9	High Similarity	NPC201373
0.9	High Similarity	NPC471799
0.8986	High Similarity	NPC145498
0.8971	High Similarity	NPC208999
0.8904	High Similarity	NPC205455
0.8904	High Similarity	NPC72507
0.8904	High Similarity	NPC318136
0.8904	High Similarity	NPC275910
0.8904	High Similarity	NPC186191
0.8889	High Similarity	NPC122418
0.8889	High Similarity	NPC120098
0.8889	High Similarity	NPC265328
0.8889	High Similarity	NPC134330
0.8889	High Similarity	NPC27765
0.8889	High Similarity	NPC189883
0.8889	High Similarity	NPC290598
0.8889	High Similarity	NPC73875
0.8889	High Similarity	NPC129165
0.8889	High Similarity	NPC30590
0.8889	High Similarity	NPC265588
0.8873	High Similarity	NPC471797
0.8857	High Similarity	NPC242001
0.8857	High Similarity	NPC167706
0.8824	High Similarity	NPC197805
0.8767	High Similarity	NPC40394
0.8767	High Similarity	NPC34177
0.8767	High Similarity	NPC91594
0.8767	High Similarity	NPC472805
0.8767	High Similarity	NPC101475
0.8767	High Similarity	NPC157996
0.8767	High Similarity	NPC90979
0.875	High Similarity	NPC141071
0.875	High Similarity	NPC257347
0.875	High Similarity	NPC471723
0.875	High Similarity	NPC477923
0.875	High Similarity	NPC66566
0.8714	High Similarity	NPC92801
0.8696	High Similarity	NPC32055
0.8696	High Similarity	NPC216460
0.8684	High Similarity	NPC87489
0.8676	High Similarity	NPC286669
0.8676	High Similarity	NPC222366
0.8676	High Similarity	NPC476039
0.8657	High Similarity	NPC225415
0.8649	High Similarity	NPC300499
0.8649	High Similarity	NPC470396
0.8649	High Similarity	NPC474989
0.8649	High Similarity	NPC196753
0.8649	High Similarity	NPC98386
0.8649	High Similarity	NPC230295
0.8649	High Similarity	NPC158662
0.8649	High Similarity	NPC22955
0.8649	High Similarity	NPC99168
0.8649	High Similarity	NPC253807
0.863	High Similarity	NPC300324
0.863	High Similarity	NPC113733
0.863	High Similarity	NPC106364
0.863	High Similarity	NPC240604
0.863	High Similarity	NPC237460
0.8592	High Similarity	NPC164022
0.8571	High Similarity	NPC82538
0.8571	High Similarity	NPC210323
0.8571	High Similarity	NPC237795
0.8553	High Similarity	NPC476646
0.8553	High Similarity	NPC6707
0.8533	High Similarity	NPC53744
0.8533	High Similarity	NPC1319
0.8533	High Similarity	NPC291379
0.8514	High Similarity	NPC477924
0.8514	High Similarity	NPC470758
0.8514	High Similarity	NPC470711
0.8514	High Similarity	NPC130136
0.8493	Intermediate Similarity	NPC285893
0.8493	Intermediate Similarity	NPC28657
0.8493	Intermediate Similarity	NPC288035
0.8493	Intermediate Similarity	NPC230301
0.8493	Intermediate Similarity	NPC162742
0.8493	Intermediate Similarity	NPC134847
0.8493	Intermediate Similarity	NPC22105
0.8493	Intermediate Similarity	NPC136188
0.8493	Intermediate Similarity	NPC304309
0.8472	Intermediate Similarity	NPC68443
0.8462	Intermediate Similarity	NPC231310
0.8451	Intermediate Similarity	NPC34834
0.8442	Intermediate Similarity	NPC202389
0.8442	Intermediate Similarity	NPC201852
0.8442	Intermediate Similarity	NPC20853
0.8429	Intermediate Similarity	NPC2648
0.8429	Intermediate Similarity	NPC96484
0.8429	Intermediate Similarity	NPC94192
0.8421	Intermediate Similarity	NPC295131
0.8421	Intermediate Similarity	NPC287749
0.8421	Intermediate Similarity	NPC96362
0.8421	Intermediate Similarity	NPC236112
0.84	Intermediate Similarity	NPC18603
0.84	Intermediate Similarity	NPC302041
0.84	Intermediate Similarity	NPC307965
0.84	Intermediate Similarity	NPC11908
0.84	Intermediate Similarity	NPC167037
0.84	Intermediate Similarity	NPC312328
0.84	Intermediate Similarity	NPC138621
0.84	Intermediate Similarity	NPC83351
0.84	Intermediate Similarity	NPC167891
0.84	Intermediate Similarity	NPC244385
0.84	Intermediate Similarity	NPC148977
0.84	Intermediate Similarity	NPC85346
0.84	Intermediate Similarity	NPC65897
0.84	Intermediate Similarity	NPC6978
0.84	Intermediate Similarity	NPC76931
0.84	Intermediate Similarity	NPC285761
0.8382	Intermediate Similarity	NPC290367
0.8378	Intermediate Similarity	NPC321016
0.8378	Intermediate Similarity	NPC107059
0.8378	Intermediate Similarity	NPC321381
0.8378	Intermediate Similarity	NPC477925
0.8378	Intermediate Similarity	NPC470749
0.8378	Intermediate Similarity	NPC253190
0.8378	Intermediate Similarity	NPC274079
0.8356	Intermediate Similarity	NPC201048
0.8356	Intermediate Similarity	NPC469534
0.8356	Intermediate Similarity	NPC469533
0.8356	Intermediate Similarity	NPC476366
0.8356	Intermediate Similarity	NPC469593
0.8333	Intermediate Similarity	NPC474789
0.8333	Intermediate Similarity	NPC52108
0.8312	Intermediate Similarity	NPC116202
0.8312	Intermediate Similarity	NPC249423
0.8312	Intermediate Similarity	NPC142163
0.8312	Intermediate Similarity	NPC242350
0.8312	Intermediate Similarity	NPC474531
0.831	Intermediate Similarity	NPC471560
0.831	Intermediate Similarity	NPC476431
0.8289	Intermediate Similarity	NPC209430
0.8289	Intermediate Similarity	NPC30986
0.8289	Intermediate Similarity	NPC472463
0.8289	Intermediate Similarity	NPC273410
0.8289	Intermediate Similarity	NPC80530
0.8267	Intermediate Similarity	NPC155986
0.8267	Intermediate Similarity	NPC198968
0.8267	Intermediate Similarity	NPC34019
0.8267	Intermediate Similarity	NPC318495
0.8243	Intermediate Similarity	NPC471468
0.8228	Intermediate Similarity	NPC238485
0.8228	Intermediate Similarity	NPC470077
0.8219	Intermediate Similarity	NPC130665
0.8219	Intermediate Similarity	NPC474140
0.8205	Intermediate Similarity	NPC49964
0.8205	Intermediate Similarity	NPC218616
0.8205	Intermediate Similarity	NPC304285
0.8205	Intermediate Similarity	NPC248886
0.8205	Intermediate Similarity	NPC30166
0.8205	Intermediate Similarity	NPC471408
0.8205	Intermediate Similarity	NPC73882
0.8205	Intermediate Similarity	NPC296701
0.8205	Intermediate Similarity	NPC470049
0.8205	Intermediate Similarity	NPC47763
0.8194	Intermediate Similarity	NPC45296
0.8182	Intermediate Similarity	NPC322313
0.8182	Intermediate Similarity	NPC102253
0.8182	Intermediate Similarity	NPC234193
0.8182	Intermediate Similarity	NPC22403
0.8182	Intermediate Similarity	NPC164840
0.8182	Intermediate Similarity	NPC236237
0.8182	Intermediate Similarity	NPC241290
0.8182	Intermediate Similarity	NPC209944
0.8182	Intermediate Similarity	NPC13554
0.8158	Intermediate Similarity	NPC477522
0.8158	Intermediate Similarity	NPC87604
0.8158	Intermediate Similarity	NPC474216
0.8158	Intermediate Similarity	NPC473943
0.8158	Intermediate Similarity	NPC476314
0.8143	Intermediate Similarity	NPC279434
0.8143	Intermediate Similarity	NPC149680
0.8133	Intermediate Similarity	NPC247325
0.8133	Intermediate Similarity	NPC244488
0.8133	Intermediate Similarity	NPC96319
0.8125	Intermediate Similarity	NPC318390
0.8108	Intermediate Similarity	NPC306727
0.8101	Intermediate Similarity	NPC159168
0.8101	Intermediate Similarity	NPC477818
0.8101	Intermediate Similarity	NPC253402
0.8101	Intermediate Similarity	NPC470384

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 NPC110799 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	2058
0.2-0.3	4149
0.3-0.4	1991
0.4-0.5	425
0.5-0.6	230
0.6-0.7	98
0.7-0.8	23
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8533	High Similarity	NPD7645	Phase 2
0.8493	Intermediate Similarity	NPD7339	Approved
0.8493	Intermediate Similarity	NPD6942	Approved
0.8182	Intermediate Similarity	NPD7525	Registered
0.8133	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8264	Approved
0.7722	Intermediate Similarity	NPD4748	Discontinued
0.7632	Intermediate Similarity	NPD4785	Approved
0.7632	Intermediate Similarity	NPD4784	Approved
0.76	Intermediate Similarity	NPD4243	Approved
0.76	Intermediate Similarity	NPD7152	Approved
0.76	Intermediate Similarity	NPD7151	Approved
0.76	Intermediate Similarity	NPD7150	Approved
0.759	Intermediate Similarity	NPD3618	Phase 1
0.7561	Intermediate Similarity	NPD4786	Approved
0.7558	Intermediate Similarity	NPD6079	Approved
0.7531	Intermediate Similarity	NPD3667	Approved
0.7529	Intermediate Similarity	NPD5328	Approved
0.7467	Intermediate Similarity	NPD7143	Approved
0.7467	Intermediate Similarity	NPD7144	Approved
0.7403	Intermediate Similarity	NPD6926	Approved
0.7403	Intermediate Similarity	NPD6924	Approved
0.7356	Intermediate Similarity	NPD7515	Phase 2
0.7333	Intermediate Similarity	NPD6923	Approved
0.7333	Intermediate Similarity	NPD6922	Approved
0.7215	Intermediate Similarity	NPD6933	Approved
0.7143	Intermediate Similarity	NPD3666	Approved
0.7143	Intermediate Similarity	NPD3133	Approved
0.7143	Intermediate Similarity	NPD3665	Phase 1
0.7093	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5275	Approved
0.7089	Intermediate Similarity	NPD4190	Phase 3
0.7079	Intermediate Similarity	NPD4202	Approved
0.7073	Intermediate Similarity	NPD7509	Discontinued
0.7033	Intermediate Similarity	NPD5221	Approved
0.7033	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD7748	Approved
0.6977	Remote Similarity	NPD5279	Phase 3
0.6957	Remote Similarity	NPD5173	Approved
0.6951	Remote Similarity	NPD6929	Approved
0.6951	Remote Similarity	NPD4195	Approved
0.6914	Remote Similarity	NPD6932	Approved
0.6882	Remote Similarity	NPD5290	Discontinued
0.6867	Remote Similarity	NPD6931	Approved
0.6867	Remote Similarity	NPD6930	Phase 2
0.686	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD368	Approved
0.6848	Remote Similarity	NPD4697	Phase 3
0.6829	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7145	Approved
0.6809	Remote Similarity	NPD4696	Approved
0.6809	Remote Similarity	NPD5286	Approved
0.6809	Remote Similarity	NPD5285	Approved
0.6778	Remote Similarity	NPD6411	Approved
0.6774	Remote Similarity	NPD4755	Approved
0.6774	Remote Similarity	NPD7902	Approved
0.6744	Remote Similarity	NPD3668	Phase 3
0.6737	Remote Similarity	NPD5223	Approved
0.6714	Remote Similarity	NPD342	Phase 1
0.6707	Remote Similarity	NPD5776	Phase 2
0.6707	Remote Similarity	NPD6925	Approved
0.6703	Remote Similarity	NPD6399	Phase 3
0.6702	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD7514	Phase 3
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7332	Phase 2
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6632	Remote Similarity	NPD4700	Approved
0.6632	Remote Similarity	NPD7640	Approved
0.6632	Remote Similarity	NPD7639	Approved
0.6628	Remote Similarity	NPD6695	Phase 3
0.6598	Remote Similarity	NPD5174	Approved
0.6598	Remote Similarity	NPD5175	Approved
0.6591	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5690	Phase 2
0.6588	Remote Similarity	NPD6902	Approved
0.6556	Remote Similarity	NPD4753	Phase 2
0.6556	Remote Similarity	NPD6101	Approved
0.6556	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6683	Phase 2
0.6531	Remote Similarity	NPD5141	Approved
0.6515	Remote Similarity	NPD385	Approved
0.6515	Remote Similarity	NPD384	Approved
0.6512	Remote Similarity	NPD4221	Approved
0.6512	Remote Similarity	NPD4223	Phase 3
0.65	Remote Similarity	NPD6881	Approved
0.65	Remote Similarity	NPD6899	Approved
0.6477	Remote Similarity	NPD5329	Approved
0.6477	Remote Similarity	NPD6893	Approved
0.6471	Remote Similarity	NPD4695	Discontinued
0.6465	Remote Similarity	NPD5739	Approved
0.6465	Remote Similarity	NPD6675	Approved
0.6465	Remote Similarity	NPD7128	Approved
0.6465	Remote Similarity	NPD6402	Approved
0.6452	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7900	Approved
0.6429	Remote Similarity	NPD3617	Approved
0.6429	Remote Similarity	NPD4754	Approved
0.6404	Remote Similarity	NPD7146	Approved
0.6404	Remote Similarity	NPD4519	Discontinued
0.6404	Remote Similarity	NPD7521	Approved
0.6404	Remote Similarity	NPD7334	Approved
0.6404	Remote Similarity	NPD6409	Approved
0.6404	Remote Similarity	NPD5330	Approved
0.6404	Remote Similarity	NPD4694	Approved
0.6404	Remote Similarity	NPD5280	Approved
0.6404	Remote Similarity	NPD4623	Approved
0.6404	Remote Similarity	NPD6684	Approved
0.64	Remote Similarity	NPD5697	Approved
0.6395	Remote Similarity	NPD4139	Approved
0.6395	Remote Similarity	NPD4692	Approved
0.6395	Remote Similarity	NPD6898	Phase 1
0.6389	Remote Similarity	NPD4219	Approved
0.6383	Remote Similarity	NPD4629	Approved
0.6383	Remote Similarity	NPD5210	Approved
0.6375	Remote Similarity	NPD4787	Phase 1
0.6374	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6883	Approved
0.6373	Remote Similarity	NPD7102	Approved
0.6373	Remote Similarity	NPD7290	Approved
0.6364	Remote Similarity	NPD4197	Approved
0.6337	Remote Similarity	NPD4729	Approved
0.6337	Remote Similarity	NPD6011	Approved
0.6337	Remote Similarity	NPD4730	Approved
0.6337	Remote Similarity	NPD5168	Approved
0.6337	Remote Similarity	NPD7320	Approved
0.6333	Remote Similarity	NPD7524	Approved
0.6333	Remote Similarity	NPD7750	Discontinued
0.6333	Remote Similarity	NPD3573	Approved
0.6311	Remote Similarity	NPD6617	Approved
0.6311	Remote Similarity	NPD8130	Phase 1
0.6311	Remote Similarity	NPD6650	Approved
0.6311	Remote Similarity	NPD6847	Approved
0.6311	Remote Similarity	NPD6649	Approved
0.6311	Remote Similarity	NPD6869	Approved
0.63	Remote Similarity	NPD4768	Approved
0.63	Remote Similarity	NPD4767	Approved
0.6296	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6012	Approved
0.6275	Remote Similarity	NPD6014	Approved
0.6275	Remote Similarity	NPD6373	Approved
0.6275	Remote Similarity	NPD6013	Approved
0.6275	Remote Similarity	NPD6372	Approved
0.6264	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6903	Approved
0.625	Remote Similarity	NPD6882	Approved
0.625	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD6083	Phase 2
0.625	Remote Similarity	NPD4788	Approved
0.625	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8297	Approved
0.6238	Remote Similarity	NPD5701	Approved
0.6237	Remote Similarity	NPD8035	Phase 2
0.6237	Remote Similarity	NPD8034	Phase 2
0.6237	Remote Similarity	NPD5284	Approved
0.6237	Remote Similarity	NPD5281	Approved
0.6224	Remote Similarity	NPD4159	Approved
0.6222	Remote Similarity	NPD4689	Approved
0.6222	Remote Similarity	NPD5205	Approved
0.6222	Remote Similarity	NPD4138	Approved
0.6222	Remote Similarity	NPD4693	Phase 3
0.6222	Remote Similarity	NPD4690	Approved
0.6222	Remote Similarity	NPD4688	Approved
0.6214	Remote Similarity	NPD5247	Approved
0.6214	Remote Similarity	NPD5248	Approved
0.6214	Remote Similarity	NPD5135	Approved
0.6214	Remote Similarity	NPD5251	Approved
0.6214	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5250	Approved
0.6214	Remote Similarity	NPD4634	Approved
0.6214	Remote Similarity	NPD5249	Phase 3
0.6214	Remote Similarity	NPD5169	Approved
0.6211	Remote Similarity	NPD5695	Phase 3
0.6196	Remote Similarity	NPD6051	Approved
0.619	Remote Similarity	NPD6117	Approved
0.6186	Remote Similarity	NPD4225	Approved
0.6176	Remote Similarity	NPD5128	Approved
0.617	Remote Similarity	NPD5779	Approved
0.617	Remote Similarity	NPD5778	Approved
0.6162	Remote Similarity	NPD7632	Discontinued
0.6154	Remote Similarity	NPD5216	Approved
0.6154	Remote Similarity	NPD5215	Approved
0.6154	Remote Similarity	NPD5217	Approved
0.6154	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5127	Approved
0.6145	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD6116	Phase 1
0.6117	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1696	Phase 3
0.6111	Remote Similarity	NPD1694	Approved
0.6087	Remote Similarity	NPD4722	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