NPASS Compound

Structure

NPC470832 OpenBabel07101718292D 34 37 0 0 1 0 0 0 0 0999 V2000 -2.6075 4.3514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8047 1.4946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8159 1.6437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1017 -1.3565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8292 -1.7219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5812 0.5879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9223 4.5778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6490 3.8549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2715 4.6662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2603 4.5172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7471 2.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8811 2.9888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1674 2.0852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2407 0.1679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7170 1.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9459 1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0101 2.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7170 2.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5384 3.9860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6131 2.9888 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.3950 2.7203 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.7603 3.6511 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.0151 2.4888 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6774 -0.6583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1490 0.9888 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4394 2.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6802 -0.7331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0151 1.4888 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7585 3.5913 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1490 2.9888 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1774 -1.5243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6947 3.9427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3510 3.8549 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 19 1 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 9 10 1 0 0 0 0 9 19 2 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 18 1 0 0 0 0 15 25 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 20 1 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 26 1 0 0 0 0 22 29 1 0 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 31 1 6 0 0 0 25 28 1 1 0 0 0 25 34 1 0 0 0 0 27 34 1 0 0 0 0 28 6 1 1 0 0 0 29 7 1 6 0 0 0 29 32 1 0 0 0 0 30 8 1 6 0 0 0 30 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.39
Volume:	525.735
LogP:	5.738
LogD:	4.497
LogS:	-5.383
# Rotatable Bonds:	3
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.436
Synthetic Accessibility Score:	5.206
Fsp3:	0.933
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:	-4.76
MDCK Permeability:	1.7257545550819486e-05
Pgp-inhibitor:	0.883
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.268
30% Bioavailability (F30%):	0.768

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.166
Plasma Protein Binding (PPB):	97.87906646728516%
Volume Distribution (VD):	1.274
Pgp-substrate:	3.0296361446380615%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.181
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.912
CYP2C9-inhibitor:	0.15
CYP2C9-substrate:	0.621
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.629
CYP3A4-inhibitor:	0.298
CYP3A4-substrate:	0.35

ADMET: Excretion

Clearance (CL):	6.394
Half-life (T1/2):	0.031

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.327
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.631
Skin Sensitization:	0.088
Carcinogencity:	0.006
Eye Corrosion:	0.009
Eye Irritation:	0.033
Respiratory Toxicity:	0.757

Download Data

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

Natural Product: NPC470832

Natural Product ID:	NPC470832
*Common Name:**	Sipholenol A
IUPAC Name:	(3R,5aR,6R,7S,9aR)-6-[2-[(1R)-1-hydroxy-1,4,4,6-tetramethyl-2,3,3a,5,8,8a-hexahydroazulen-5-yl]ethyl]-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydro-3H-benzo[b]oxepine-3,7-diol
Synonyms:	Sipholenol A
Standard InCHIKey:	LVWWPNAIMBYRKG-NXHAIPTASA-N
Standard InCHI:	InChI=1S/C30H52O4/c1-19-9-10-22-21(13-17-29(22,7)32)26(2,3)20(19)11-12-23-28(6)16-14-24(31)27(4,5)34-25(28)15-18-30(23,8)33/h9,20-25,31-33H,10-18H2,1-8H3/t20?,21?,22?,23-,24-,25-,28-,29-,30+/m1/s1
SMILES:	CC1=CCC2C(CCC2(C)O)C(C1CCC3C4(CCC(C(OC4CCC3(C)O)(C)C)O)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL226093
PubChem CID:	16757532
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17488128]
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19534474]
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	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	10
Others	2

Activity Type	# Activity
Cell Line	6
Individual Protein	2
NON-MOLECULAR	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1178	Cell Line	KB 3-1	Homo sapiens	IC50	=	5.0	nM	PMID[523181]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	50000.0	nM	PMID[523181]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	50000.0	nM	PMID[523183]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	44500.0	nM	PMID[523183]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	37500.0	nM	PMID[523183]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	37497.3	nM	PMID[523183]
NPT2	Others	Unspecified		IC50	=	210.0	nM	PMID[523181]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[523181]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	0.9	n.a.	PMID[523182]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	25.0	n.a.	PMID[523182]

☑ 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 NPC470832 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	191
0.1-0.2	1768
0.2-0.3	6387
0.3-0.4	15781
0.4-0.5	7290
0.5-0.6	7233
0.6-0.7	3668
0.7-0.8	358
0.8-0.85	14
0.85-0.9	5
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9655	High Similarity	NPC473258
0.8778	High Similarity	NPC210268
0.875	High Similarity	NPC470838
0.8736	High Similarity	NPC290731
0.8571	High Similarity	NPC94127
0.8539	High Similarity	NPC189777
0.8427	Intermediate Similarity	NPC476217
0.8352	Intermediate Similarity	NPC97103
0.8352	Intermediate Similarity	NPC115607
0.828	Intermediate Similarity	NPC98193
0.8125	Intermediate Similarity	NPC475033
0.8125	Intermediate Similarity	NPC475032
0.809	Intermediate Similarity	NPC110778
0.8081	Intermediate Similarity	NPC475334
0.8081	Intermediate Similarity	NPC475623
0.8081	Intermediate Similarity	NPC473694
0.8068	Intermediate Similarity	NPC473257
0.8043	Intermediate Similarity	NPC22376
0.8022	Intermediate Similarity	NPC201273
0.8	Intermediate Similarity	NPC475585
0.8	Intermediate Similarity	NPC124172
0.8	Intermediate Similarity	NPC181104
0.8	Intermediate Similarity	NPC103298
0.8	Intermediate Similarity	NPC80809
0.8	Intermediate Similarity	NPC473577
0.8	Intermediate Similarity	NPC475331
0.8	Intermediate Similarity	NPC474550
0.8	Intermediate Similarity	NPC201144
0.8	Intermediate Similarity	NPC288502
0.8	Intermediate Similarity	NPC475335
0.8	Intermediate Similarity	NPC121518
0.7957	Intermediate Similarity	NPC109744
0.7957	Intermediate Similarity	NPC105495
0.7938	Intermediate Similarity	NPC470834
0.7938	Intermediate Similarity	NPC476021
0.7938	Intermediate Similarity	NPC476040
0.7938	Intermediate Similarity	NPC474994
0.7935	Intermediate Similarity	NPC186145
0.7935	Intermediate Similarity	NPC474657
0.7935	Intermediate Similarity	NPC233744
0.7921	Intermediate Similarity	NPC60315
0.7921	Intermediate Similarity	NPC475290
0.79	Intermediate Similarity	NPC475701
0.7889	Intermediate Similarity	NPC477818
0.7889	Intermediate Similarity	NPC207013
0.7889	Intermediate Similarity	NPC193870
0.7889	Intermediate Similarity	NPC141941
0.7879	Intermediate Similarity	NPC155974
0.7872	Intermediate Similarity	NPC475751
0.7872	Intermediate Similarity	NPC473956
0.7865	Intermediate Similarity	NPC70927
0.7857	Intermediate Similarity	NPC470067
0.7857	Intermediate Similarity	NPC470066
0.7857	Intermediate Similarity	NPC216260
0.7857	Intermediate Similarity	NPC5358
0.7849	Intermediate Similarity	NPC475664
0.7826	Intermediate Similarity	NPC24277
0.7826	Intermediate Similarity	NPC6605
0.7826	Intermediate Similarity	NPC125399
0.7822	Intermediate Similarity	NPC474464
0.7802	Intermediate Similarity	NPC242016
0.7802	Intermediate Similarity	NPC127606
0.7802	Intermediate Similarity	NPC475798
0.78	Intermediate Similarity	NPC470840
0.78	Intermediate Similarity	NPC22634
0.7778	Intermediate Similarity	NPC208358
0.7778	Intermediate Similarity	NPC1272
0.7778	Intermediate Similarity	NPC30166
0.7778	Intermediate Similarity	NPC470614
0.7755	Intermediate Similarity	NPC261807
0.7755	Intermediate Similarity	NPC272451
0.7755	Intermediate Similarity	NPC316604
0.7753	Intermediate Similarity	NPC236237
0.7753	Intermediate Similarity	NPC102253
0.7753	Intermediate Similarity	NPC13554
0.7753	Intermediate Similarity	NPC322313
0.7745	Intermediate Similarity	NPC474015
0.7732	Intermediate Similarity	NPC8774
0.77	Intermediate Similarity	NPC47566
0.77	Intermediate Similarity	NPC88000
0.77	Intermediate Similarity	NPC472023
0.77	Intermediate Similarity	NPC129372
0.77	Intermediate Similarity	NPC4831
0.77	Intermediate Similarity	NPC160734
0.77	Intermediate Similarity	NPC309425
0.7684	Intermediate Similarity	NPC107189
0.7677	Intermediate Similarity	NPC280825
0.7677	Intermediate Similarity	NPC275865
0.7677	Intermediate Similarity	NPC476895
0.7677	Intermediate Similarity	NPC234287
0.7677	Intermediate Similarity	NPC309493
0.766	Intermediate Similarity	NPC470542
0.766	Intermediate Similarity	NPC133588
0.766	Intermediate Similarity	NPC474668
0.766	Intermediate Similarity	NPC473436
0.7653	Intermediate Similarity	NPC210717
0.7653	Intermediate Similarity	NPC288970
0.7653	Intermediate Similarity	NPC103165
0.7653	Intermediate Similarity	NPC72204
0.7653	Intermediate Similarity	NPC227583
0.7653	Intermediate Similarity	NPC12103
0.7653	Intermediate Similarity	NPC253115
0.7653	Intermediate Similarity	NPC98457
0.7653	Intermediate Similarity	NPC304899
0.7647	Intermediate Similarity	NPC471111
0.7647	Intermediate Similarity	NPC41886
0.764	Intermediate Similarity	NPC1319
0.764	Intermediate Similarity	NPC273410
0.764	Intermediate Similarity	NPC80530
0.7634	Intermediate Similarity	NPC94462
0.7634	Intermediate Similarity	NPC145245
0.7634	Intermediate Similarity	NPC139724
0.7634	Intermediate Similarity	NPC121981
0.7629	Intermediate Similarity	NPC127718
0.7629	Intermediate Similarity	NPC65402
0.7629	Intermediate Similarity	NPC39453
0.7624	Intermediate Similarity	NPC470972
0.7624	Intermediate Similarity	NPC136816
0.7609	Intermediate Similarity	NPC255882
0.7609	Intermediate Similarity	NPC209802
0.7604	Intermediate Similarity	NPC97404
0.7604	Intermediate Similarity	NPC41554
0.76	Intermediate Similarity	NPC324598
0.76	Intermediate Similarity	NPC471242
0.76	Intermediate Similarity	NPC7341
0.76	Intermediate Similarity	NPC473200
0.7582	Intermediate Similarity	NPC7988
0.7579	Intermediate Similarity	NPC470361
0.7576	Intermediate Similarity	NPC26307
0.7576	Intermediate Similarity	NPC476893
0.7573	Intermediate Similarity	NPC26798
0.7573	Intermediate Similarity	NPC242748
0.7556	Intermediate Similarity	NPC71535
0.7556	Intermediate Similarity	NPC26117
0.7556	Intermediate Similarity	NPC78545
0.7556	Intermediate Similarity	NPC236112
0.7553	Intermediate Similarity	NPC476948
0.7553	Intermediate Similarity	NPC271967
0.7551	Intermediate Similarity	NPC476894
0.7551	Intermediate Similarity	NPC292178
0.7551	Intermediate Similarity	NPC86893
0.7549	Intermediate Similarity	NPC472821
0.7549	Intermediate Similarity	NPC31907
0.7549	Intermediate Similarity	NPC155010
0.7549	Intermediate Similarity	NPC120123
0.7549	Intermediate Similarity	NPC189852
0.7549	Intermediate Similarity	NPC472252
0.7549	Intermediate Similarity	NPC131479
0.7549	Intermediate Similarity	NPC470839
0.7549	Intermediate Similarity	NPC245280
0.7549	Intermediate Similarity	NPC157659
0.7549	Intermediate Similarity	NPC213190
0.7549	Intermediate Similarity	NPC286969
0.7549	Intermediate Similarity	NPC16520
0.7549	Intermediate Similarity	NPC114874
0.7549	Intermediate Similarity	NPC473020
0.7549	Intermediate Similarity	NPC8039
0.7549	Intermediate Similarity	NPC211879
0.7549	Intermediate Similarity	NPC160583
0.7529	Intermediate Similarity	NPC471781
0.7528	Intermediate Similarity	NPC167037
0.7528	Intermediate Similarity	NPC477817
0.7528	Intermediate Similarity	NPC285761
0.7528	Intermediate Similarity	NPC244385
0.7528	Intermediate Similarity	NPC6978
0.7528	Intermediate Similarity	NPC138621
0.7528	Intermediate Similarity	NPC477819
0.7527	Intermediate Similarity	NPC474349
0.7527	Intermediate Similarity	NPC318390
0.7527	Intermediate Similarity	NPC474189
0.7526	Intermediate Similarity	NPC119379
0.7526	Intermediate Similarity	NPC137461
0.7525	Intermediate Similarity	NPC474022
0.7525	Intermediate Similarity	NPC73385
0.7525	Intermediate Similarity	NPC475617
0.7525	Intermediate Similarity	NPC476896
0.7524	Intermediate Similarity	NPC128133
0.75	Intermediate Similarity	NPC216420
0.75	Intermediate Similarity	NPC132635
0.75	Intermediate Similarity	NPC226642
0.75	Intermediate Similarity	NPC329596
0.75	Intermediate Similarity	NPC232023
0.75	Intermediate Similarity	NPC211135
0.75	Intermediate Similarity	NPC291484
0.75	Intermediate Similarity	NPC85095
0.75	Intermediate Similarity	NPC80561
0.75	Intermediate Similarity	NPC3345
0.75	Intermediate Similarity	NPC470068
0.75	Intermediate Similarity	NPC471340
0.75	Intermediate Similarity	NPC11216
0.75	Intermediate Similarity	NPC126969
0.75	Intermediate Similarity	NPC473469
0.75	Intermediate Similarity	NPC204188
0.75	Intermediate Similarity	NPC102426
0.75	Intermediate Similarity	NPC295668
0.75	Intermediate Similarity	NPC300179
0.7476	Intermediate Similarity	NPC187400
0.7476	Intermediate Similarity	NPC273879
0.7476	Intermediate Similarity	NPC221562
0.7476	Intermediate Similarity	NPC165033

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 NPC470832 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	2278
0.2-0.3	4232
0.3-0.4	1757
0.4-0.5	340
0.5-0.6	213
0.6-0.7	148
0.7-0.8	4
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
0.7753	Intermediate Similarity	NPD7525	Registered
0.7553	Intermediate Similarity	NPD7524	Approved
0.7419	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6695	Phase 3
0.7303	Intermediate Similarity	NPD6933	Approved
0.7143	Intermediate Similarity	NPD7327	Approved
0.7143	Intermediate Similarity	NPD7328	Approved
0.7111	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD7516	Approved
0.7079	Intermediate Similarity	NPD6926	Approved
0.7079	Intermediate Similarity	NPD6924	Approved
0.701	Intermediate Similarity	NPD7750	Discontinued
0.701	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6942	Approved
0.7	Intermediate Similarity	NPD7339	Approved
0.699	Remote Similarity	NPD7638	Approved
0.6989	Remote Similarity	NPD6930	Phase 2
0.6989	Remote Similarity	NPD6931	Approved
0.6937	Remote Similarity	NPD4632	Approved
0.6923	Remote Similarity	NPD7639	Approved
0.6923	Remote Similarity	NPD7640	Approved
0.6882	Remote Similarity	NPD6929	Approved
0.687	Remote Similarity	NPD8294	Approved
0.687	Remote Similarity	NPD8377	Approved
0.6854	Remote Similarity	NPD4243	Approved
0.6852	Remote Similarity	NPD6412	Phase 2
0.6848	Remote Similarity	NPD6932	Approved
0.6832	Remote Similarity	NPD4202	Approved
0.681	Remote Similarity	NPD8335	Approved
0.681	Remote Similarity	NPD8379	Approved
0.681	Remote Similarity	NPD8378	Approved
0.681	Remote Similarity	NPD8296	Approved
0.681	Remote Similarity	NPD8380	Approved
0.681	Remote Similarity	NPD8033	Approved
0.6809	Remote Similarity	NPD7509	Discontinued
0.6809	Remote Similarity	NPD4748	Discontinued
0.6759	Remote Similarity	NPD6675	Approved
0.6759	Remote Similarity	NPD7128	Approved
0.6759	Remote Similarity	NPD6402	Approved
0.6759	Remote Similarity	NPD5739	Approved
0.6733	Remote Similarity	NPD7087	Discontinued
0.6731	Remote Similarity	NPD4755	Approved
0.6724	Remote Similarity	NPD6054	Approved
0.6724	Remote Similarity	NPD6319	Approved
0.6724	Remote Similarity	NPD6059	Approved
0.6703	Remote Similarity	NPD4784	Approved
0.6703	Remote Similarity	NPD4785	Approved
0.6702	Remote Similarity	NPD6683	Phase 2
0.6702	Remote Similarity	NPD7645	Phase 2
0.6698	Remote Similarity	NPD5344	Discontinued
0.6696	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD5776	Phase 2
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD7150	Approved
0.6667	Remote Similarity	NPD7152	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD6925	Approved
0.6667	Remote Similarity	NPD7151	Approved
0.6636	Remote Similarity	NPD6881	Approved
0.6636	Remote Similarity	NPD7320	Approved
0.6636	Remote Similarity	NPD6899	Approved
0.6634	Remote Similarity	NPD3168	Discontinued
0.6633	Remote Similarity	NPD6893	Approved
0.6632	Remote Similarity	NPD7514	Phase 3
0.6629	Remote Similarity	NPD6923	Approved
0.6629	Remote Similarity	NPD6922	Approved
0.661	Remote Similarity	NPD6370	Approved
0.6609	Remote Similarity	NPD6009	Approved
0.6604	Remote Similarity	NPD5285	Approved
0.6604	Remote Similarity	NPD4696	Approved
0.6604	Remote Similarity	NPD4700	Approved
0.6604	Remote Similarity	NPD5286	Approved
0.6596	Remote Similarity	NPD7145	Approved
0.6583	Remote Similarity	NPD7507	Approved
0.6577	Remote Similarity	NPD6373	Approved
0.6577	Remote Similarity	NPD6372	Approved
0.6556	Remote Similarity	NPD7143	Approved
0.6556	Remote Similarity	NPD7144	Approved
0.6555	Remote Similarity	NPD7604	Phase 2
0.6545	Remote Similarity	NPD5701	Approved
0.6545	Remote Similarity	NPD5697	Approved
0.6542	Remote Similarity	NPD5223	Approved
0.6535	Remote Similarity	NPD5328	Approved
0.6531	Remote Similarity	NPD4786	Approved
0.6525	Remote Similarity	NPD6015	Approved
0.6525	Remote Similarity	NPD6016	Approved
0.6525	Remote Similarity	NPD5983	Phase 2
0.6518	Remote Similarity	NPD7290	Approved
0.6518	Remote Similarity	NPD6883	Approved
0.6518	Remote Similarity	NPD6371	Approved
0.6518	Remote Similarity	NPD7102	Approved
0.6505	Remote Similarity	NPD6399	Phase 3
0.65	Remote Similarity	NPD7492	Approved
0.6486	Remote Similarity	NPD6011	Approved
0.6481	Remote Similarity	NPD5224	Approved
0.6481	Remote Similarity	NPD4633	Approved
0.6481	Remote Similarity	NPD5211	Phase 2
0.6481	Remote Similarity	NPD5226	Approved
0.6481	Remote Similarity	NPD5225	Approved
0.6471	Remote Similarity	NPD5988	Approved
0.646	Remote Similarity	NPD6869	Approved
0.646	Remote Similarity	NPD8130	Phase 1
0.646	Remote Similarity	NPD6649	Approved
0.646	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6617	Approved
0.646	Remote Similarity	NPD6650	Approved
0.646	Remote Similarity	NPD6847	Approved
0.6458	Remote Similarity	NPD7332	Phase 2
0.6455	Remote Similarity	NPD6008	Approved
0.6452	Remote Similarity	NPD5275	Approved
0.6452	Remote Similarity	NPD4190	Phase 3
0.6446	Remote Similarity	NPD6616	Approved
0.6446	Remote Similarity	NPD6336	Discontinued
0.6444	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6012	Approved
0.6429	Remote Similarity	NPD6013	Approved
0.6429	Remote Similarity	NPD6014	Approved
0.6423	Remote Similarity	NPD7319	Approved
0.6422	Remote Similarity	NPD5174	Approved
0.6422	Remote Similarity	NPD4754	Approved
0.6422	Remote Similarity	NPD5175	Approved
0.6415	Remote Similarity	NPD6083	Phase 2
0.6415	Remote Similarity	NPD6084	Phase 2
0.6408	Remote Similarity	NPD6079	Approved
0.6404	Remote Similarity	NPD6882	Approved
0.64	Remote Similarity	NPD3618	Phase 1
0.6393	Remote Similarity	NPD7078	Approved
0.6393	Remote Similarity	NPD8293	Discontinued
0.6392	Remote Similarity	NPD6902	Approved
0.6392	Remote Similarity	NPD6898	Phase 1
0.6389	Remote Similarity	NPD4159	Approved
0.6373	Remote Similarity	NPD4753	Phase 2
0.6373	Remote Similarity	NPD6051	Approved
0.6364	Remote Similarity	NPD5141	Approved
0.6364	Remote Similarity	NPD3665	Phase 1
0.6364	Remote Similarity	NPD3133	Approved
0.6364	Remote Similarity	NPD3666	Approved
0.6355	Remote Similarity	NPD4225	Approved
0.6354	Remote Similarity	NPD4195	Approved
0.6341	Remote Similarity	NPD6033	Approved
0.6341	Remote Similarity	NPD7736	Approved
0.633	Remote Similarity	NPD7632	Discontinued
0.6327	Remote Similarity	NPD3667	Approved
0.6306	Remote Similarity	NPD4768	Approved
0.6306	Remote Similarity	NPD4767	Approved
0.6296	Remote Similarity	NPD6648	Approved
0.6289	Remote Similarity	NPD6928	Phase 2
0.6283	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6067	Discontinued
0.6261	Remote Similarity	NPD6053	Discontinued
0.625	Remote Similarity	NPD8035	Phase 2
0.625	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD8034	Phase 2
0.6226	Remote Similarity	NPD5695	Phase 3
0.6207	Remote Similarity	NPD8133	Approved
0.6195	Remote Similarity	NPD5128	Approved
0.6195	Remote Similarity	NPD4730	Approved
0.6195	Remote Similarity	NPD4729	Approved
0.6195	Remote Similarity	NPD6686	Approved
0.619	Remote Similarity	NPD8171	Discontinued
0.6186	Remote Similarity	NPD7115	Discovery
0.6168	Remote Similarity	NPD5221	Approved
0.6168	Remote Similarity	NPD4697	Phase 3
0.6168	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5222	Approved
0.6162	Remote Similarity	NPD4221	Approved
0.6162	Remote Similarity	NPD4223	Phase 3
0.6161	Remote Similarity	NPD5357	Phase 1
0.6139	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5329	Approved
0.6139	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6335	Approved
0.6111	Remote Similarity	NPD5173	Approved
0.6105	Remote Similarity	NPD8264	Approved
0.6102	Remote Similarity	NPD6274	Approved
0.61	Remote Similarity	NPD4788	Approved
0.6087	Remote Similarity	NPD5250	Approved
0.6087	Remote Similarity	NPD5169	Approved
0.6087	Remote Similarity	NPD5248	Approved
0.6087	Remote Similarity	NPD5135	Approved
0.6087	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5251	Approved
0.6087	Remote Similarity	NPD5249	Phase 3
0.6087	Remote Similarity	NPD5247	Approved
0.6083	Remote Similarity	NPD7101	Approved
0.6083	Remote Similarity	NPD7100	Approved
0.6078	Remote Similarity	NPD7521	Approved
0.6078	Remote Similarity	NPD6684	Approved
0.6078	Remote Similarity	NPD5279	Phase 3
0.6078	Remote Similarity	NPD5330	Approved
0.6078	Remote Similarity	NPD6409	Approved
0.6078	Remote Similarity	NPD7146	Approved
0.6078	Remote Similarity	NPD7334	Approved
0.6075	Remote Similarity	NPD4629	Approved
0.6075	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5210	Approved
0.6055	Remote Similarity	NPD5696	Approved
0.6053	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.605	Remote Similarity	NPD6317	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