NPASS Compound

Structure

NPC470838 OpenBabel07101718292D 35 38 0 0 1 0 0 0 0 0999 V2000 -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 -2.6075 -4.3514 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 -2.4585 -5.3402 0.0000 O 0 0 0 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 26 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 17 1 0 0 0 0 14 25 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 19 1 0 0 0 0 18 31 2 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 6 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 32 1 1 0 0 0 25 28 1 6 0 0 0 25 35 1 0 0 0 0 27 35 1 0 0 0 0 28 5 1 6 0 0 0 29 6 1 1 0 0 0 29 33 1 0 0 0 0 30 7 1 1 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.37
Volume:	531.888
LogP:	4.398
LogD:	3.949
LogS:	-4.906
# Rotatable Bonds:	4
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.472
Synthetic Accessibility Score:	5.345
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.778
MDCK Permeability:	4.01086981582921e-05
Pgp-inhibitor:	0.969
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.303

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.212
Plasma Protein Binding (PPB):	92.6346206665039%
Volume Distribution (VD):	1.11
Pgp-substrate:	4.290105819702148%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.138
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.865
CYP2C9-inhibitor:	0.116
CYP2C9-substrate:	0.544
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.378
CYP3A4-inhibitor:	0.382
CYP3A4-substrate:	0.396

ADMET: Excretion

Clearance (CL):	4.568
Half-life (T1/2):	0.077

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.566
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.62
Carcinogencity:	0.011
Eye Corrosion:	0.036
Eye Irritation:	0.085
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC470838

Natural Product ID:	NPC470838
*Common Name:**	(1R,E)-5-(2-((3R,5Ar,6R,7S,9Ar)-3,7-Dihydroxy-2,2,5A,7-Tetramethyl-Decahydrobenzo[B]Oxepin-6-Yl)Ethyl)-1-Hydroxy-1,4,4-Trimethyl-1,2,3,3A,4,5,8,8A-Octahydroazulene-6-Carbaldehyde
IUPAC Name:	(3R)-7-[2-[(3R,5aR,6R,7S,9aR)-3,7-dihydroxy-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydro-3H-benzo[b]oxepin-6-yl]ethyl]-3-hydroxy-3,8,8-trimethyl-1,2,3a,4,7,8a-hexahydroazulene-6-carbaldehyde
Synonyms:
Standard InCHIKey:	BDNMFPOVAWCGRX-NXHAIPTASA-N
Standard InCHI:	InChI=1S/C30H50O5/c1-26(2)20(19(18-31)8-9-22-21(26)12-16-29(22,6)33)10-11-23-28(5)15-13-24(32)27(3,4)35-25(28)14-17-30(23,7)34/h8,18,20-25,32-34H,9-17H2,1-7H3/t20?,21?,22?,23-,24-,25-,28-,29-,30+/m1/s1
SMILES:	O=CC1=CCC2C(C(C1CC[C@H]1[C@@](C)(O)CC[C@@H]3[C@]1(C)CC[C@H](C(O3)(C)C)O)(C)C)CC[C@@]2(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL226197
PubChem CID:	16736856
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	6

Activity Type	# Activity
Cell Line	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[478968]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	50000.0	nM	PMID[478968]
NPT2	Others	Unspecified		IC50	=	2850.0	nM	PMID[478968]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[478968]

☑ 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 NPC470838 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	212
0.1-0.2	1389
0.2-0.3	5486
0.3-0.4	12649
0.4-0.5	9268
0.5-0.6	7492
0.6-0.7	5704
0.7-0.8	491
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.875	High Similarity	NPC470832
0.8725	High Similarity	NPC470839
0.8485	Intermediate Similarity	NPC473258
0.8235	Intermediate Similarity	NPC470834
0.8095	Intermediate Similarity	NPC470840
0.8058	Intermediate Similarity	NPC272451
0.8	Intermediate Similarity	NPC237190
0.7961	Intermediate Similarity	NPC91439
0.7941	Intermediate Similarity	NPC111015
0.7925	Intermediate Similarity	NPC22388
0.7876	Intermediate Similarity	NPC298278
0.787	Intermediate Similarity	NPC60315
0.7857	Intermediate Similarity	NPC178981
0.7857	Intermediate Similarity	NPC317210
0.785	Intermediate Similarity	NPC473694
0.785	Intermediate Similarity	NPC475623
0.785	Intermediate Similarity	NPC475334
0.7788	Intermediate Similarity	NPC472400
0.7788	Intermediate Similarity	NPC477580
0.7788	Intermediate Similarity	NPC326542
0.7778	Intermediate Similarity	NPC121518
0.7778	Intermediate Similarity	NPC181104
0.7778	Intermediate Similarity	NPC103298
0.7778	Intermediate Similarity	NPC474550
0.7778	Intermediate Similarity	NPC473577
0.7778	Intermediate Similarity	NPC288502
0.7778	Intermediate Similarity	NPC475331
0.7778	Intermediate Similarity	NPC475335
0.7778	Intermediate Similarity	NPC201144
0.7778	Intermediate Similarity	NPC80809
0.7778	Intermediate Similarity	NPC475585
0.7768	Intermediate Similarity	NPC234042
0.7768	Intermediate Similarity	NPC207251
0.7768	Intermediate Similarity	NPC152117
0.7748	Intermediate Similarity	NPC6206
0.7748	Intermediate Similarity	NPC76084
0.7745	Intermediate Similarity	NPC210268
0.7736	Intermediate Similarity	NPC154072
0.7727	Intermediate Similarity	NPC217201
0.7719	Intermediate Similarity	NPC196931
0.7706	Intermediate Similarity	NPC260268
0.7706	Intermediate Similarity	NPC85829
0.7706	Intermediate Similarity	NPC171137
0.7706	Intermediate Similarity	NPC150531
0.7706	Intermediate Similarity	NPC152695
0.7706	Intermediate Similarity	NPC214264
0.7706	Intermediate Similarity	NPC296945
0.7706	Intermediate Similarity	NPC48733
0.7706	Intermediate Similarity	NPC97202
0.7706	Intermediate Similarity	NPC49958
0.7706	Intermediate Similarity	NPC202167
0.7706	Intermediate Similarity	NPC475290
0.7706	Intermediate Similarity	NPC476027
0.7706	Intermediate Similarity	NPC302607
0.7706	Intermediate Similarity	NPC319077
0.7706	Intermediate Similarity	NPC50692
0.7699	Intermediate Similarity	NPC260665
0.7699	Intermediate Similarity	NPC472757
0.7699	Intermediate Similarity	NPC962
0.7699	Intermediate Similarity	NPC250109
0.7699	Intermediate Similarity	NPC194100
0.7677	Intermediate Similarity	NPC290731
0.7672	Intermediate Similarity	NPC472667
0.7658	Intermediate Similarity	NPC11710
0.7658	Intermediate Similarity	NPC170221
0.7658	Intermediate Similarity	NPC10064
0.7652	Intermediate Similarity	NPC156252
0.7647	Intermediate Similarity	NPC191684
0.7636	Intermediate Similarity	NPC220229
0.7636	Intermediate Similarity	NPC475060
0.7636	Intermediate Similarity	NPC83744
0.7632	Intermediate Similarity	NPC74727
0.7615	Intermediate Similarity	NPC204833
0.7615	Intermediate Similarity	NPC209502
0.7593	Intermediate Similarity	NPC473424
0.7589	Intermediate Similarity	NPC197428
0.7586	Intermediate Similarity	NPC472758
0.7586	Intermediate Similarity	NPC171905
0.7586	Intermediate Similarity	NPC472397
0.7586	Intermediate Similarity	NPC475372
0.7586	Intermediate Similarity	NPC471125
0.7586	Intermediate Similarity	NPC146280
0.7586	Intermediate Similarity	NPC124676
0.7573	Intermediate Similarity	NPC94127
0.757	Intermediate Similarity	NPC112167
0.757	Intermediate Similarity	NPC167974
0.7568	Intermediate Similarity	NPC65941
0.7568	Intermediate Similarity	NPC329417
0.7565	Intermediate Similarity	NPC266728
0.7565	Intermediate Similarity	NPC49492
0.7565	Intermediate Similarity	NPC154363
0.7565	Intermediate Similarity	NPC190286
0.7565	Intermediate Similarity	NPC234858
0.7565	Intermediate Similarity	NPC471127
0.7563	Intermediate Similarity	NPC129992
0.7547	Intermediate Similarity	NPC475032
0.7547	Intermediate Similarity	NPC475033
0.7545	Intermediate Similarity	NPC149047
0.7545	Intermediate Similarity	NPC470980
0.7525	Intermediate Similarity	NPC189777
0.7524	Intermediate Similarity	NPC472824
0.7524	Intermediate Similarity	NPC279974
0.7522	Intermediate Similarity	NPC158523
0.7522	Intermediate Similarity	NPC475937
0.7521	Intermediate Similarity	NPC22628
0.7521	Intermediate Similarity	NPC255081
0.7521	Intermediate Similarity	NPC475041
0.7521	Intermediate Similarity	NPC5991
0.7521	Intermediate Similarity	NPC275696
0.7521	Intermediate Similarity	NPC312536
0.7521	Intermediate Similarity	NPC471108
0.7521	Intermediate Similarity	NPC5989
0.75	Intermediate Similarity	NPC163004
0.75	Intermediate Similarity	NPC470257
0.75	Intermediate Similarity	NPC10721
0.75	Intermediate Similarity	NPC473656
0.7479	Intermediate Similarity	NPC257017
0.7479	Intermediate Similarity	NPC162009
0.7478	Intermediate Similarity	NPC238667
0.7478	Intermediate Similarity	NPC216665
0.7478	Intermediate Similarity	NPC178289
0.7477	Intermediate Similarity	NPC477916
0.7477	Intermediate Similarity	NPC119036
0.7458	Intermediate Similarity	NPC472004
0.7458	Intermediate Similarity	NPC143755
0.7458	Intermediate Similarity	NPC475885
0.7458	Intermediate Similarity	NPC79579
0.7458	Intermediate Similarity	NPC471128
0.7458	Intermediate Similarity	NPC145182
0.7458	Intermediate Similarity	NPC157252
0.7458	Intermediate Similarity	NPC471126
0.7456	Intermediate Similarity	NPC470063
0.7455	Intermediate Similarity	NPC149124
0.7455	Intermediate Similarity	NPC75531
0.7455	Intermediate Similarity	NPC471293
0.7451	Intermediate Similarity	NPC476704
0.7451	Intermediate Similarity	NPC193360
0.7438	Intermediate Similarity	NPC250556
0.7438	Intermediate Similarity	NPC469750
0.7436	Intermediate Similarity	NPC288679
0.7436	Intermediate Similarity	NPC153440
0.7434	Intermediate Similarity	NPC179642
0.7434	Intermediate Similarity	NPC101450
0.7434	Intermediate Similarity	NPC250956
0.7434	Intermediate Similarity	NPC153036
0.7434	Intermediate Similarity	NPC235077
0.7434	Intermediate Similarity	NPC163314
0.7431	Intermediate Similarity	NPC470972
0.7431	Intermediate Similarity	NPC477915
0.7431	Intermediate Similarity	NPC162973
0.7429	Intermediate Similarity	NPC67831
0.7429	Intermediate Similarity	NPC196485
0.7429	Intermediate Similarity	NPC103527
0.7429	Intermediate Similarity	NPC174051
0.7429	Intermediate Similarity	NPC245972
0.7426	Intermediate Similarity	NPC476217
0.7426	Intermediate Similarity	NPC232156
0.7426	Intermediate Similarity	NPC94755
0.7417	Intermediate Similarity	NPC473979
0.7414	Intermediate Similarity	NPC469794
0.7414	Intermediate Similarity	NPC470793
0.7414	Intermediate Similarity	NPC138372
0.7414	Intermediate Similarity	NPC106228
0.7414	Intermediate Similarity	NPC72772
0.7411	Intermediate Similarity	NPC258323
0.7411	Intermediate Similarity	NPC306265
0.7411	Intermediate Similarity	NPC88701
0.7411	Intermediate Similarity	NPC472217
0.7411	Intermediate Similarity	NPC472219
0.7411	Intermediate Similarity	NPC472825
0.7411	Intermediate Similarity	NPC177064
0.7411	Intermediate Similarity	NPC472218
0.7407	Intermediate Similarity	NPC470074
0.7407	Intermediate Similarity	NPC144956
0.7407	Intermediate Similarity	NPC83709
0.7404	Intermediate Similarity	NPC155304
0.7395	Intermediate Similarity	NPC46570
0.7395	Intermediate Similarity	NPC472401
0.7395	Intermediate Similarity	NPC52839
0.7395	Intermediate Similarity	NPC310511
0.7391	Intermediate Similarity	NPC477944
0.7391	Intermediate Similarity	NPC108721
0.7391	Intermediate Similarity	NPC71889
0.7391	Intermediate Similarity	NPC73300
0.7387	Intermediate Similarity	NPC96377
0.7387	Intermediate Similarity	NPC278628
0.7387	Intermediate Similarity	NPC469874
0.7387	Intermediate Similarity	NPC470309
0.7387	Intermediate Similarity	NPC231530
0.7383	Intermediate Similarity	NPC18509
0.7383	Intermediate Similarity	NPC108078
0.7383	Intermediate Similarity	NPC190554
0.7379	Intermediate Similarity	NPC97103
0.7379	Intermediate Similarity	NPC472983
0.7379	Intermediate Similarity	NPC115607
0.7379	Intermediate Similarity	NPC32830
0.7377	Intermediate Similarity	NPC179412
0.7377	Intermediate Similarity	NPC471356
0.7373	Intermediate Similarity	NPC5292
0.7373	Intermediate Similarity	NPC473203

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 NPC470838 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1922
0.2-0.3	4175
0.3-0.4	2025
0.4-0.5	420
0.5-0.6	214
0.6-0.7	174
0.7-0.8	37
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
0.7699	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD4202	Approved
0.7477	Intermediate Similarity	NPD6412	Phase 2
0.7458	Intermediate Similarity	NPD6054	Approved
0.7458	Intermediate Similarity	NPD6319	Approved
0.7456	Intermediate Similarity	NPD8297	Approved
0.7438	Intermediate Similarity	NPD7507	Approved
0.7434	Intermediate Similarity	NPD4634	Approved
0.7411	Intermediate Similarity	NPD6881	Approved
0.7411	Intermediate Similarity	NPD6899	Approved
0.7407	Intermediate Similarity	NPD5286	Approved
0.7407	Intermediate Similarity	NPD4696	Approved
0.7407	Intermediate Similarity	NPD5285	Approved
0.7387	Intermediate Similarity	NPD7128	Approved
0.7387	Intermediate Similarity	NPD6675	Approved
0.7387	Intermediate Similarity	NPD6402	Approved
0.7387	Intermediate Similarity	NPD5739	Approved
0.7383	Intermediate Similarity	NPD4755	Approved
0.735	Intermediate Similarity	NPD6009	Approved
0.7339	Intermediate Similarity	NPD5223	Approved
0.7333	Intermediate Similarity	NPD6370	Approved
0.7321	Intermediate Similarity	NPD5697	Approved
0.7315	Intermediate Similarity	NPD7638	Approved
0.7311	Intermediate Similarity	NPD6059	Approved
0.7281	Intermediate Similarity	NPD7102	Approved
0.7281	Intermediate Similarity	NPD6371	Approved
0.7281	Intermediate Similarity	NPD6883	Approved
0.7281	Intermediate Similarity	NPD7290	Approved
0.7273	Intermediate Similarity	NPD4633	Approved
0.7273	Intermediate Similarity	NPD5225	Approved
0.7273	Intermediate Similarity	NPD5226	Approved
0.7273	Intermediate Similarity	NPD5224	Approved
0.7273	Intermediate Similarity	NPD5211	Phase 2
0.7273	Intermediate Similarity	NPD7604	Phase 2
0.7258	Intermediate Similarity	NPD7319	Approved
0.7257	Intermediate Similarity	NPD7320	Approved
0.7257	Intermediate Similarity	NPD6011	Approved
0.725	Intermediate Similarity	NPD6015	Approved
0.725	Intermediate Similarity	NPD5983	Phase 2
0.725	Intermediate Similarity	NPD6016	Approved
0.7248	Intermediate Similarity	NPD7639	Approved
0.7248	Intermediate Similarity	NPD4700	Approved
0.7248	Intermediate Similarity	NPD7640	Approved
0.7238	Intermediate Similarity	NPD6079	Approved
0.7217	Intermediate Similarity	NPD8130	Phase 1
0.7217	Intermediate Similarity	NPD6617	Approved
0.7217	Intermediate Similarity	NPD6869	Approved
0.7217	Intermediate Similarity	NPD6650	Approved
0.7217	Intermediate Similarity	NPD6847	Approved
0.7217	Intermediate Similarity	NPD6649	Approved
0.7213	Intermediate Similarity	NPD7492	Approved
0.7212	Intermediate Similarity	NPD5328	Approved
0.7207	Intermediate Similarity	NPD5174	Approved
0.7207	Intermediate Similarity	NPD5175	Approved
0.7193	Intermediate Similarity	NPD6372	Approved
0.7193	Intermediate Similarity	NPD6014	Approved
0.7193	Intermediate Similarity	NPD6012	Approved
0.7193	Intermediate Similarity	NPD6013	Approved
0.7193	Intermediate Similarity	NPD6373	Approved
0.719	Intermediate Similarity	NPD5988	Approved
0.7168	Intermediate Similarity	NPD5701	Approved
0.7155	Intermediate Similarity	NPD6882	Approved
0.7154	Intermediate Similarity	NPD6336	Discontinued
0.7154	Intermediate Similarity	NPD6616	Approved
0.7143	Intermediate Similarity	NPD5141	Approved
0.713	Intermediate Similarity	NPD4697	Phase 3
0.7097	Intermediate Similarity	NPD7078	Approved
0.7087	Intermediate Similarity	NPD3618	Phase 1
0.708	Intermediate Similarity	NPD6008	Approved
0.7069	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6084	Phase 2
0.7064	Intermediate Similarity	NPD6083	Phase 2
0.7059	Intermediate Similarity	NPD3665	Phase 1
0.7059	Intermediate Similarity	NPD3666	Approved
0.7059	Intermediate Similarity	NPD3133	Approved
0.7054	Intermediate Similarity	NPD4754	Approved
0.7048	Intermediate Similarity	NPD4753	Phase 2
0.704	Intermediate Similarity	NPD7736	Approved
0.7	Intermediate Similarity	NPD7328	Approved
0.7	Intermediate Similarity	NPD7327	Approved
0.6972	Remote Similarity	NPD5222	Approved
0.6972	Remote Similarity	NPD5221	Approved
0.6972	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.696	Remote Similarity	NPD8293	Discontinued
0.6957	Remote Similarity	NPD5128	Approved
0.6957	Remote Similarity	NPD6686	Approved
0.6957	Remote Similarity	NPD4730	Approved
0.6957	Remote Similarity	NPD4729	Approved
0.6942	Remote Similarity	NPD7516	Approved
0.693	Remote Similarity	NPD4768	Approved
0.693	Remote Similarity	NPD4767	Approved
0.6917	Remote Similarity	NPD7115	Discovery
0.6909	Remote Similarity	NPD5173	Approved
0.6905	Remote Similarity	NPD6033	Approved
0.6897	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4786	Approved
0.6881	Remote Similarity	NPD5695	Phase 3
0.6881	Remote Similarity	NPD4629	Approved
0.6881	Remote Similarity	NPD5210	Approved
0.6864	Remote Similarity	NPD6053	Discontinued
0.6863	Remote Similarity	NPD4221	Approved
0.6863	Remote Similarity	NPD4223	Phase 3
0.686	Remote Similarity	NPD6335	Approved
0.6855	Remote Similarity	NPD6067	Discontinued
0.6852	Remote Similarity	NPD6399	Phase 3
0.6838	Remote Similarity	NPD5250	Approved
0.6838	Remote Similarity	NPD5249	Phase 3
0.6838	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5251	Approved
0.6838	Remote Similarity	NPD5247	Approved
0.6838	Remote Similarity	NPD5135	Approved
0.6838	Remote Similarity	NPD5169	Approved
0.6838	Remote Similarity	NPD5248	Approved
0.6833	Remote Similarity	NPD6274	Approved
0.6832	Remote Similarity	NPD7525	Registered
0.6827	Remote Similarity	NPD5329	Approved
0.6803	Remote Similarity	NPD7101	Approved
0.6803	Remote Similarity	NPD7100	Approved
0.6796	Remote Similarity	NPD4788	Approved
0.678	Remote Similarity	NPD5215	Approved
0.678	Remote Similarity	NPD5216	Approved
0.678	Remote Similarity	NPD5217	Approved
0.678	Remote Similarity	NPD5127	Approved
0.6777	Remote Similarity	NPD6317	Approved
0.6762	Remote Similarity	NPD5279	Phase 3
0.6762	Remote Similarity	NPD6684	Approved
0.6762	Remote Similarity	NPD7334	Approved
0.6762	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7146	Approved
0.6762	Remote Similarity	NPD6409	Approved
0.6762	Remote Similarity	NPD5330	Approved
0.6762	Remote Similarity	NPD7521	Approved
0.6762	Remote Similarity	NPD5690	Phase 2
0.6748	Remote Similarity	NPD8377	Approved
0.6748	Remote Similarity	NPD8294	Approved
0.6731	Remote Similarity	NPD4197	Approved
0.6727	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5344	Discontinued
0.6724	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6313	Approved
0.6721	Remote Similarity	NPD6314	Approved
0.6699	Remote Similarity	NPD3667	Approved
0.6698	Remote Similarity	NPD7524	Approved
0.6696	Remote Similarity	NPD5696	Approved
0.6696	Remote Similarity	NPD4225	Approved
0.6694	Remote Similarity	NPD8335	Approved
0.6694	Remote Similarity	NPD7503	Approved
0.6694	Remote Similarity	NPD8033	Approved
0.6694	Remote Similarity	NPD8379	Approved
0.6694	Remote Similarity	NPD8380	Approved
0.6694	Remote Similarity	NPD8296	Approved
0.6694	Remote Similarity	NPD8378	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6636	Remote Similarity	NPD6903	Approved
0.6636	Remote Similarity	NPD7748	Approved
0.6636	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5167	Approved
0.6607	Remote Similarity	NPD7902	Approved
0.6606	Remote Similarity	NPD8035	Phase 2
0.6606	Remote Similarity	NPD8034	Phase 2
0.6606	Remote Similarity	NPD5281	Approved
0.6606	Remote Similarity	NPD7515	Phase 2
0.6606	Remote Similarity	NPD5284	Approved
0.6604	Remote Similarity	NPD4693	Phase 3
0.6604	Remote Similarity	NPD4138	Approved
0.6604	Remote Similarity	NPD4694	Approved
0.6604	Remote Similarity	NPD4689	Approved
0.6604	Remote Similarity	NPD4688	Approved
0.6604	Remote Similarity	NPD5205	Approved
0.6604	Remote Similarity	NPD5280	Approved
0.6604	Remote Similarity	NPD4690	Approved
0.6574	Remote Similarity	NPD6904	Approved
0.6574	Remote Similarity	NPD6673	Approved
0.6574	Remote Similarity	NPD6080	Approved
0.6571	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6908	Approved
0.656	Remote Similarity	NPD6909	Approved
0.656	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD4522	Approved
0.6529	Remote Similarity	NPD8133	Approved
0.6514	Remote Similarity	NPD6698	Approved
0.6514	Remote Similarity	NPD46	Approved
0.6509	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5282	Discontinued
0.6481	Remote Similarity	NPD6672	Approved
0.6481	Remote Similarity	NPD5737	Approved
0.6476	Remote Similarity	NPD6695	Phase 3
0.6455	Remote Similarity	NPD6050	Approved
0.6436	Remote Similarity	NPD6933	Approved
0.6423	Remote Similarity	NPD6868	Approved
0.6412	Remote Similarity	NPD5956	Approved
0.6408	Remote Similarity	NPD4195	Approved
0.6387	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5168	Approved
0.6381	Remote Similarity	NPD6435	Approved
0.6364	Remote Similarity	NPD5785	Approved
0.6364	Remote Similarity	NPD5692	Phase 3
0.6364	Remote Similarity	NPD4096	Approved
0.6348	Remote Similarity	NPD6648	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