NPASS Compound

Structure

CID13823 OpenBabel06191715342D 28 29 0 0 1 0 0 0 0 0999 V2000 -6.6973 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8601 1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1858 -1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8372 -1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1858 0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0229 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3486 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5115 -1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5115 -2.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5115 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3486 0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8601 0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3486 -0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8372 -2.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5115 0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6743 -2.9000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8372 -2.4167 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6743 -0.9667 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6743 0.9667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8372 0.4833 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8372 -0.4833 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3486 1.9333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6743 -3.8667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6743 -2.9000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6743 -1.9333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6743 1.9333 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 2 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 14 2 0 0 0 0 9 17 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 23 1 0 0 0 0 15 17 1 0 0 0 0 16 20 1 0 0 0 0 17 24 1 1 0 0 0 18 25 1 1 0 0 0 19 22 1 6 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 6 0 0 0 21 22 1 6 0 0 0 21 28 1 0 0 0 0 22 18 1 6 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.24
Volume:	414.151
LogP:	1.65
LogD:	1.684
LogS:	-3.415
# Rotatable Bonds:	9
TPSA:	113.68
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.299
Synthetic Accessibility Score:	5.206
Fsp3:	0.636
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.12
MDCK Permeability:	3.7291836633812636e-05
Pgp-inhibitor:	0.927
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.974
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.331
Plasma Protein Binding (PPB):	88.0510025024414%
Volume Distribution (VD):	0.942
Pgp-substrate:	11.332130432128906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.105
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.113
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.12

ADMET: Excretion

Clearance (CL):	5.808
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.28
Human Hepatotoxicity (H-HT):	0.993
Drug-inuced Liver Injury (DILI):	0.885
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.974
Maximum Recommended Daily Dose:	0.999
Skin Sensitization:	0.845
Carcinogencity:	0.248
Eye Corrosion:	0.004
Eye Irritation:	0.051
Respiratory Toxicity:	0.99

Download Data

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

Natural Product: NPC13823

Natural Product ID:	NPC13823
*Common Name:**	Arthrobotrisin B
IUPAC Name:	(1S,2R,5S,6R)-6-[(1S,2E,4S,6E)-1,4-dihydroxy-3,7,11-trimethyldodeca-2,6,10-trienyl]-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol
Synonyms:	arthrobotrisin B
Standard InCHIKey:	VTOBGWHJIIZDHV-XMCVGHNMSA-N
Standard InCHI:	InChI=1S/C22H34O6/c1-13(2)6-5-7-14(3)8-9-17(24)15(4)10-18(25)22-19(26)11-16(12-23)20(27)21(22)28-22/h6,8,10-11,17-21,23-27H,5,7,9,12H2,1-4H3/b14-8+,15-10+/t17-,18-,19-,20+,21-,22+/m0/s1
SMILES:	OCC1=C[C@H](O)[C@@]2([C@H]([C@@H]1O)O2)[C@H](/C=C(/[C@H](C/C=C(/CCC=C(C)C)C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1814572
PubChem CID:	53360482
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
NPO6706	Arthrobotrys oligospora	Species	Orbiliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21568306]
NPO6706	Arthrobotrys oligospora	Species	Orbiliaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1271	Organism	Bacillus sp.	Bacillus sp.	IZ	=	4.7	mm	PMID[511282]
NPT1271	Organism	Bacillus sp.	Bacillus sp.	IZ	=	8.0	mm	PMID[511282]

☑ 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 NPC13823 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	184
0.1-0.2	1944
0.2-0.3	6097
0.3-0.4	16611
0.4-0.5	10590
0.5-0.6	5934
0.6-0.7	1205
0.7-0.8	113
0.8-0.85	14
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC68119
0.8421	Intermediate Similarity	NPC24590
0.8333	Intermediate Similarity	NPC476703
0.8313	Intermediate Similarity	NPC255143
0.8205	Intermediate Similarity	NPC170148
0.8193	Intermediate Similarity	NPC298595
0.814	Intermediate Similarity	NPC191323
0.8108	Intermediate Similarity	NPC82337
0.8023	Intermediate Similarity	NPC49783
0.8	Intermediate Similarity	NPC477089
0.7955	Intermediate Similarity	NPC119379
0.7949	Intermediate Similarity	NPC190859
0.7821	Intermediate Similarity	NPC476709
0.7816	Intermediate Similarity	NPC115607
0.7816	Intermediate Similarity	NPC128066
0.7802	Intermediate Similarity	NPC261807
0.7763	Intermediate Similarity	NPC305698
0.7722	Intermediate Similarity	NPC471525
0.7692	Intermediate Similarity	NPC57664
0.7692	Intermediate Similarity	NPC103165
0.7692	Intermediate Similarity	NPC210717
0.7683	Intermediate Similarity	NPC476701
0.7674	Intermediate Similarity	NPC281316
0.7662	Intermediate Similarity	NPC304690
0.7662	Intermediate Similarity	NPC74722
0.7662	Intermediate Similarity	NPC239373
0.7662	Intermediate Similarity	NPC329989
0.7654	Intermediate Similarity	NPC40049
0.7647	Intermediate Similarity	NPC83702
0.7632	Intermediate Similarity	NPC73603
0.7632	Intermediate Similarity	NPC259299
0.7619	Intermediate Similarity	NPC477390
0.7619	Intermediate Similarity	NPC477385
0.7614	Intermediate Similarity	NPC97103
0.76	Intermediate Similarity	NPC473722
0.7564	Intermediate Similarity	NPC129630
0.7558	Intermediate Similarity	NPC290731
0.7556	Intermediate Similarity	NPC137461
0.7553	Intermediate Similarity	NPC476896
0.7534	Intermediate Similarity	NPC258788
0.7531	Intermediate Similarity	NPC236228
0.7531	Intermediate Similarity	NPC256720
0.7528	Intermediate Similarity	NPC197107
0.75	Intermediate Similarity	NPC326310
0.75	Intermediate Similarity	NPC288970
0.75	Intermediate Similarity	NPC472995
0.75	Intermediate Similarity	NPC474894
0.75	Intermediate Similarity	NPC72204
0.7474	Intermediate Similarity	NPC39996
0.7471	Intermediate Similarity	NPC196381
0.7471	Intermediate Similarity	NPC476217
0.7444	Intermediate Similarity	NPC114389
0.7444	Intermediate Similarity	NPC41554
0.7444	Intermediate Similarity	NPC97404
0.7439	Intermediate Similarity	NPC477426
0.7439	Intermediate Similarity	NPC477427
0.7439	Intermediate Similarity	NPC474826
0.7439	Intermediate Similarity	NPC477425
0.7436	Intermediate Similarity	NPC472947
0.7436	Intermediate Similarity	NPC16964
0.7416	Intermediate Similarity	NPC470361
0.7412	Intermediate Similarity	NPC259858
0.7412	Intermediate Similarity	NPC471408
0.7396	Intermediate Similarity	NPC118902
0.7396	Intermediate Similarity	NPC469980
0.7396	Intermediate Similarity	NPC104161
0.7391	Intermediate Similarity	NPC8774
0.7391	Intermediate Similarity	NPC469583
0.7386	Intermediate Similarity	NPC189777
0.7386	Intermediate Similarity	NPC476948
0.7386	Intermediate Similarity	NPC245004
0.7381	Intermediate Similarity	NPC236707
0.7375	Intermediate Similarity	NPC220939
0.7375	Intermediate Similarity	NPC265485
0.7368	Intermediate Similarity	NPC471200
0.734	Intermediate Similarity	NPC476895
0.7333	Intermediate Similarity	NPC291484
0.7333	Intermediate Similarity	NPC11216
0.7333	Intermediate Similarity	NPC80561
0.7333	Intermediate Similarity	NPC3952
0.7333	Intermediate Similarity	NPC477684
0.7333	Intermediate Similarity	NPC3345
0.7333	Intermediate Similarity	NPC329596
0.7333	Intermediate Similarity	NPC204188
0.7326	Intermediate Similarity	NPC231601
0.7312	Intermediate Similarity	NPC472997
0.7312	Intermediate Similarity	NPC472996
0.7312	Intermediate Similarity	NPC227583
0.7312	Intermediate Similarity	NPC98457
0.7312	Intermediate Similarity	NPC90583
0.7312	Intermediate Similarity	NPC12103
0.7308	Intermediate Similarity	NPC272961
0.7303	Intermediate Similarity	NPC248312
0.7303	Intermediate Similarity	NPC474668
0.7294	Intermediate Similarity	NPC471270
0.7294	Intermediate Similarity	NPC476646
0.7283	Intermediate Similarity	NPC65402
0.7283	Intermediate Similarity	NPC127718
0.7273	Intermediate Similarity	NPC267027
0.7273	Intermediate Similarity	NPC311163
0.7273	Intermediate Similarity	NPC477387
0.7273	Intermediate Similarity	NPC125399
0.7273	Intermediate Similarity	NPC6391
0.7273	Intermediate Similarity	NPC477389
0.7263	Intermediate Similarity	NPC38855
0.7263	Intermediate Similarity	NPC64348
0.726	Intermediate Similarity	NPC226848
0.7253	Intermediate Similarity	NPC302584
0.7253	Intermediate Similarity	NPC210268
0.725	Intermediate Similarity	NPC23954
0.7241	Intermediate Similarity	NPC78673
0.7241	Intermediate Similarity	NPC160517
0.7241	Intermediate Similarity	NPC186155
0.7234	Intermediate Similarity	NPC182811
0.7234	Intermediate Similarity	NPC472998
0.7234	Intermediate Similarity	NPC473244
0.7234	Intermediate Similarity	NPC476893
0.7229	Intermediate Similarity	NPC84360
0.7222	Intermediate Similarity	NPC20946
0.7222	Intermediate Similarity	NPC246028
0.7222	Intermediate Similarity	NPC187785
0.7222	Intermediate Similarity	NPC161560
0.7222	Intermediate Similarity	NPC477917
0.7222	Intermediate Similarity	NPC259875
0.7204	Intermediate Similarity	NPC476720
0.72	Intermediate Similarity	NPC68679
0.72	Intermediate Similarity	NPC87335
0.72	Intermediate Similarity	NPC321867
0.72	Intermediate Similarity	NPC207007
0.7191	Intermediate Similarity	NPC477386
0.7191	Intermediate Similarity	NPC233744
0.7191	Intermediate Similarity	NPC477388
0.7179	Intermediate Similarity	NPC163290
0.7176	Intermediate Similarity	NPC100697
0.7176	Intermediate Similarity	NPC96362
0.7176	Intermediate Similarity	NPC471266
0.7176	Intermediate Similarity	NPC95124
0.7174	Intermediate Similarity	NPC310013
0.7172	Intermediate Similarity	NPC266514
0.7158	Intermediate Similarity	NPC312325
0.7158	Intermediate Similarity	NPC274458
0.7143	Intermediate Similarity	NPC181838
0.7143	Intermediate Similarity	NPC52755
0.7143	Intermediate Similarity	NPC287339
0.7143	Intermediate Similarity	NPC476314
0.7143	Intermediate Similarity	NPC137345
0.7128	Intermediate Similarity	NPC211810
0.7128	Intermediate Similarity	NPC284194
0.7128	Intermediate Similarity	NPC221801
0.7128	Intermediate Similarity	NPC471765
0.7126	Intermediate Similarity	NPC477978
0.7126	Intermediate Similarity	NPC185605
0.7123	Intermediate Similarity	NPC52012
0.7113	Intermediate Similarity	NPC470972
0.7111	Intermediate Similarity	NPC309656
0.7111	Intermediate Similarity	NPC133588
0.7111	Intermediate Similarity	NPC67872
0.7108	Intermediate Similarity	NPC229655
0.7108	Intermediate Similarity	NPC265588
0.7097	Intermediate Similarity	NPC96736
0.7097	Intermediate Similarity	NPC473258
0.7097	Intermediate Similarity	NPC178949
0.7097	Intermediate Similarity	NPC472416
0.7097	Intermediate Similarity	NPC472360
0.7093	Intermediate Similarity	NPC249423
0.7093	Intermediate Similarity	NPC246621
0.7093	Intermediate Similarity	NPC16090
0.7083	Intermediate Similarity	NPC269713
0.7083	Intermediate Similarity	NPC79303
0.7083	Intermediate Similarity	NPC272223
0.7079	Intermediate Similarity	NPC475684
0.7079	Intermediate Similarity	NPC61527
0.7079	Intermediate Similarity	NPC237344
0.7079	Intermediate Similarity	NPC261266
0.7073	Intermediate Similarity	NPC474280
0.7067	Intermediate Similarity	NPC66020
0.7065	Intermediate Similarity	NPC91251
0.7065	Intermediate Similarity	NPC476705
0.7065	Intermediate Similarity	NPC208839
0.7065	Intermediate Similarity	NPC475441
0.7059	Intermediate Similarity	NPC291260
0.7059	Intermediate Similarity	NPC471537
0.7053	Intermediate Similarity	NPC347923
0.7053	Intermediate Similarity	NPC205143
0.7053	Intermediate Similarity	NPC476057
0.7053	Intermediate Similarity	NPC240372
0.7051	Intermediate Similarity	NPC311736
0.7045	Intermediate Similarity	NPC469809
0.7045	Intermediate Similarity	NPC474047
0.7045	Intermediate Similarity	NPC185568
0.7037	Intermediate Similarity	NPC242992
0.7037	Intermediate Similarity	NPC306085
0.7037	Intermediate Similarity	NPC477087
0.7037	Intermediate Similarity	NPC477086
0.7024	Intermediate Similarity	NPC477924
0.7024	Intermediate Similarity	NPC130136
0.7024	Intermediate Similarity	NPC474278
0.7021	Intermediate Similarity	NPC476894
0.7021	Intermediate Similarity	NPC240838
0.7011	Intermediate Similarity	NPC253364

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 NPC13823 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	2445
0.2-0.3	3846
0.3-0.4	2004
0.4-0.5	549
0.5-0.6	113
0.6-0.7	22
0.7-0.8	3
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
0.7368	Intermediate Similarity	NPD5344	Discontinued
0.72	Intermediate Similarity	NPD368	Approved
0.7	Intermediate Similarity	NPD7524	Approved
0.6957	Remote Similarity	NPD7838	Discovery
0.6957	Remote Similarity	NPD46	Approved
0.6957	Remote Similarity	NPD6698	Approved
0.6907	Remote Similarity	NPD6648	Approved
0.6854	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD342	Phase 1
0.6774	Remote Similarity	NPD3168	Discontinued
0.6742	Remote Similarity	NPD6695	Phase 3
0.6548	Remote Similarity	NPD4732	Discontinued
0.6526	Remote Similarity	NPD7983	Approved
0.6477	Remote Similarity	NPD7645	Phase 2
0.6458	Remote Similarity	NPD5778	Approved
0.6458	Remote Similarity	NPD5779	Approved
0.6452	Remote Similarity	NPD7750	Discontinued
0.6404	Remote Similarity	NPD7525	Registered
0.6404	Remote Similarity	NPD6931	Approved
0.6404	Remote Similarity	NPD6930	Phase 2
0.6395	Remote Similarity	NPD8264	Approved
0.6374	Remote Similarity	NPD6110	Phase 1
0.6364	Remote Similarity	NPD585	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4225	Approved
0.6292	Remote Similarity	NPD6929	Approved
0.6277	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7115	Discovery
0.625	Remote Similarity	NPD5357	Phase 1
0.6226	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7332	Phase 2
0.6222	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7514	Phase 3
0.6186	Remote Similarity	NPD7087	Discontinued
0.6176	Remote Similarity	NPD4159	Approved
0.6173	Remote Similarity	NPD371	Approved
0.6154	Remote Similarity	NPD6902	Approved
0.6139	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD6933	Approved
0.6117	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4251	Approved
0.6105	Remote Similarity	NPD4250	Approved
0.6078	Remote Similarity	NPD7640	Approved
0.6078	Remote Similarity	NPD7639	Approved
0.6067	Remote Similarity	NPD5776	Phase 2
0.6067	Remote Similarity	NPD6925	Approved
0.6064	Remote Similarity	NPD6893	Approved
0.6053	Remote Similarity	NPD8515	Approved
0.6053	Remote Similarity	NPD8517	Approved
0.6053	Remote Similarity	NPD8516	Approved
0.6053	Remote Similarity	NPD8513	Phase 3
0.6044	Remote Similarity	NPD4821	Approved
0.6044	Remote Similarity	NPD4820	Approved
0.6044	Remote Similarity	NPD4819	Approved
0.6044	Remote Similarity	NPD4822	Approved
0.6023	Remote Similarity	NPD7339	Approved
0.6023	Remote Similarity	NPD6942	Approved
0.6022	Remote Similarity	NPD7154	Phase 3
0.6019	Remote Similarity	NPD6371	Approved
0.6	Remote Similarity	NPD7145	Approved
0.6	Remote Similarity	NPD4249	Approved
0.6	Remote Similarity	NPD4268	Approved
0.6	Remote Similarity	NPD4271	Approved
0.598	Remote Similarity	NPD7638	Approved
0.5978	Remote Similarity	NPD6898	Phase 1
0.5963	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.593	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD7327	Approved
0.5929	Remote Similarity	NPD7328	Approved
0.5913	Remote Similarity	NPD8033	Approved
0.5909	Remote Similarity	NPD6924	Approved
0.5909	Remote Similarity	NPD6926	Approved
0.5904	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD6932	Approved
0.5877	Remote Similarity	NPD7516	Approved
0.5872	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.587	Remote Similarity	NPD7509	Discontinued
0.5859	Remote Similarity	NPD7637	Suspended
0.5833	Remote Similarity	NPD4265	Approved
0.5826	Remote Similarity	NPD8294	Approved
0.5826	Remote Similarity	NPD8377	Approved
0.5824	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD6101	Approved
0.5816	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD8074	Phase 3
0.5794	Remote Similarity	NPD6640	Phase 3
0.5784	Remote Similarity	NPD7839	Suspended
0.5776	Remote Similarity	NPD8378	Approved
0.5776	Remote Similarity	NPD8380	Approved
0.5776	Remote Similarity	NPD8296	Approved
0.5776	Remote Similarity	NPD8379	Approved
0.5776	Remote Similarity	NPD7503	Approved
0.5776	Remote Similarity	NPD8335	Approved
0.5766	Remote Similarity	NPD6430	Approved
0.5766	Remote Similarity	NPD6429	Approved
0.5761	Remote Similarity	NPD6683	Phase 2
0.5758	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD6412	Phase 2
0.5729	Remote Similarity	NPD1696	Phase 3
0.57	Remote Similarity	NPD6411	Approved
0.5688	Remote Similarity	NPD6686	Approved
0.5684	Remote Similarity	NPD5362	Discontinued
0.566	Remote Similarity	NPD5211	Phase 2
0.5648	Remote Similarity	NPD7128	Approved
0.5648	Remote Similarity	NPD6675	Approved
0.5648	Remote Similarity	NPD5739	Approved
0.5648	Remote Similarity	NPD6402	Approved
0.5644	Remote Similarity	NPD6399	Phase 3
0.5636	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4786	Approved
0.5625	Remote Similarity	NPD6053	Discontinued
0.5625	Remote Similarity	NPD8297	Approved
0.561	Remote Similarity	NPD1145	Discontinued
0.56	Remote Similarity	NPD9410	Clinical (unspecified phase)

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