NPASS Compound

Structure

NPC475458 OpenBabel07101718182D 21 23 0 0 1 0 0 0 0 0999 V2000 1.3156 -1.9713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 -0.1623 -1.5438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6032 -1.2695 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8540 -1.1163 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6967 -1.6547 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 15 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 21 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 1 1 6 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 10 18 1 6 0 0 0 11 12 1 0 0 0 0 11 21 1 6 0 0 0 12 17 1 1 0 0 0 13 15 1 0 0 0 0 13 17 1 1 0 0 0 14 15 1 0 0 0 0 14 16 1 1 0 0 0 14 19 1 0 0 0 0 16 17 1 1 0 0 0 17 20 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.21
Volume:	312.08
LogP:	2.229
LogD:	2.641
LogS:	-3.504
# Rotatable Bonds:	1
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	4.944
Fsp3:	1.0
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:	-4.779
MDCK Permeability:	1.443223845853936e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.945
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.053
30% Bioavailability (F30%):	0.836

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.146
Plasma Protein Binding (PPB):	49.45893478393555%
Volume Distribution (VD):	1.265
Pgp-substrate:	43.417564392089844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.454
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.825
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.21
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.249

ADMET: Excretion

Clearance (CL):	4.563
Half-life (T1/2):	0.57

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.354
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.91
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.619
Carcinogencity:	0.009
Eye Corrosion:	0.019
Eye Irritation:	0.051
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC475458

Natural Product ID:	NPC475458
*Common Name:**	7-Hydroxy-10-Methoxydeacetyldihydrobotrydial
IUPAC Name:	(1R,3S,3aR,5R,5aR,6S,8aS,8bR)-6-methoxy-2,2,5,8a-tetramethyl-3,3a,4,5,5a,6,7,8-octahydro-1H-acenaphthylene-1,3,8b-triol
Synonyms:
Standard InCHIKey:	HPDGBLQRXWCICU-MAKLDSAESA-N
Standard InCHI:	InChI=1S/C17H30O4/c1-9-8-10(18)13-15(2,3)14(19)16(4)7-6-11(21-5)12(9)17(13,16)20/h9-14,18-20H,6-8H2,1-5H3/t9-,10+,11+,12-,13+,14-,16+,17-/m1/s1
SMILES:	CC1CC(C2C(C(C3(C2(C1C(CC3)OC)O)C)O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506010
PubChem CID:	44575377
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001670] Tertiary alcohols

*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
NPO32658	geniculosporium sp.	Species	Xylariaceae	Eukaryota	n.a.	isolated from the marine red alga Polysiphonia	n.a.	PMID[15787444]
NPO32658	geniculosporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917307]

☑ 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	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Unit	Reference
NPT1234	Organism	Chlorella fusca	Chlorella fusca	IZ	=	mm	PMID[519478]
NPT1230	Organism	Bacillus megaterium	Bacillus megaterium	IZ	=	mm	PMID[519478]
NPT1231	Organism	Microbotryum violaceum	Microbotryum violaceum	IZ	=	mm	PMID[519478]

☑ 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 NPC475458 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	392
0.1-0.2	4233
0.2-0.3	13768
0.3-0.4	11172
0.4-0.5	5250
0.5-0.6	4996
0.6-0.7	2336
0.7-0.8	475
0.8-0.85	43
0.85-0.9	27
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9265	High Similarity	NPC474756
0.9155	High Similarity	NPC304499
0.8933	High Similarity	NPC474714
0.8873	High Similarity	NPC1340
0.8873	High Similarity	NPC187471
0.8873	High Similarity	NPC252182
0.8873	High Similarity	NPC470071
0.8784	High Similarity	NPC185915
0.8784	High Similarity	NPC105208
0.8784	High Similarity	NPC302578
0.8784	High Similarity	NPC128951
0.8784	High Similarity	NPC192046
0.8784	High Similarity	NPC476233
0.8784	High Similarity	NPC477227
0.8767	High Similarity	NPC317242
0.8732	High Similarity	NPC232925
0.8732	High Similarity	NPC251201
0.8732	High Similarity	NPC63588
0.8667	High Similarity	NPC67657
0.8667	High Similarity	NPC18857
0.8649	High Similarity	NPC163597
0.8592	High Similarity	NPC66407
0.8592	High Similarity	NPC477820
0.8553	High Similarity	NPC287452
0.8553	High Similarity	NPC269333
0.8529	High Similarity	NPC236099
0.8529	High Similarity	NPC209686
0.8529	High Similarity	NPC249078
0.8514	High Similarity	NPC243027
0.8514	High Similarity	NPC196136
0.8514	High Similarity	NPC158208
0.8493	Intermediate Similarity	NPC470610
0.8493	Intermediate Similarity	NPC153719
0.8421	Intermediate Similarity	NPC471769
0.8378	Intermediate Similarity	NPC228994
0.8378	Intermediate Similarity	NPC192501
0.8378	Intermediate Similarity	NPC10476
0.8378	Intermediate Similarity	NPC48795
0.8375	Intermediate Similarity	NPC266651
0.8356	Intermediate Similarity	NPC127094
0.8354	Intermediate Similarity	NPC69953
0.8312	Intermediate Similarity	NPC476176
0.8312	Intermediate Similarity	NPC477282
0.8312	Intermediate Similarity	NPC81074
0.8267	Intermediate Similarity	NPC131584
0.8267	Intermediate Similarity	NPC139765
0.8228	Intermediate Similarity	NPC475388
0.8219	Intermediate Similarity	NPC192192
0.8205	Intermediate Similarity	NPC66766
0.8205	Intermediate Similarity	NPC117137
0.8205	Intermediate Similarity	NPC16449
0.8182	Intermediate Similarity	NPC471045
0.8182	Intermediate Similarity	NPC147993
0.8171	Intermediate Similarity	NPC5943
0.8169	Intermediate Similarity	NPC44122
0.8133	Intermediate Similarity	NPC470151
0.8125	Intermediate Similarity	NPC478054
0.8125	Intermediate Similarity	NPC232023
0.8108	Intermediate Similarity	NPC100586
0.8108	Intermediate Similarity	NPC157422
0.8108	Intermediate Similarity	NPC109457
0.8082	Intermediate Similarity	NPC107919
0.8082	Intermediate Similarity	NPC254037
0.8082	Intermediate Similarity	NPC129829
0.8052	Intermediate Similarity	NPC474574
0.8052	Intermediate Similarity	NPC133596
0.8052	Intermediate Similarity	NPC64081
0.8052	Intermediate Similarity	NPC11907
0.8049	Intermediate Similarity	NPC471240
0.8049	Intermediate Similarity	NPC131365
0.8028	Intermediate Similarity	NPC472946
0.8026	Intermediate Similarity	NPC472950
0.8026	Intermediate Similarity	NPC472952
0.8025	Intermediate Similarity	NPC320824
0.8	Intermediate Similarity	NPC154043
0.8	Intermediate Similarity	NPC60018
0.8	Intermediate Similarity	NPC202688
0.8	Intermediate Similarity	NPC470611
0.8	Intermediate Similarity	NPC296734
0.7973	Intermediate Similarity	NPC282454
0.7952	Intermediate Similarity	NPC210658
0.7952	Intermediate Similarity	NPC161928
0.7952	Intermediate Similarity	NPC472396
0.7945	Intermediate Similarity	NPC472741
0.7922	Intermediate Similarity	NPC470145
0.7901	Intermediate Similarity	NPC29342
0.7901	Intermediate Similarity	NPC2572
0.7895	Intermediate Similarity	NPC477508
0.7887	Intermediate Similarity	NPC159654
0.7887	Intermediate Similarity	NPC118937
0.7887	Intermediate Similarity	NPC167995
0.7887	Intermediate Similarity	NPC281540
0.7882	Intermediate Similarity	NPC279329
0.7875	Intermediate Similarity	NPC473257
0.7875	Intermediate Similarity	NPC73515
0.7867	Intermediate Similarity	NPC157777
0.7867	Intermediate Similarity	NPC131506
0.7857	Intermediate Similarity	NPC185547
0.7857	Intermediate Similarity	NPC128475
0.7857	Intermediate Similarity	NPC95804
0.7838	Intermediate Similarity	NPC470833
0.7831	Intermediate Similarity	NPC6605
0.7831	Intermediate Similarity	NPC155531
0.7831	Intermediate Similarity	NPC215968
0.7831	Intermediate Similarity	NPC121981
0.7831	Intermediate Similarity	NPC201273
0.7808	Intermediate Similarity	NPC48079
0.7808	Intermediate Similarity	NPC475884
0.7808	Intermediate Similarity	NPC473230
0.7808	Intermediate Similarity	NPC63190
0.7805	Intermediate Similarity	NPC474156
0.7805	Intermediate Similarity	NPC256567
0.7805	Intermediate Similarity	NPC86238
0.7794	Intermediate Similarity	NPC236588
0.7792	Intermediate Similarity	NPC231680
0.7792	Intermediate Similarity	NPC91387
0.7792	Intermediate Similarity	NPC186851
0.7792	Intermediate Similarity	NPC270306
0.7791	Intermediate Similarity	NPC293609
0.7791	Intermediate Similarity	NPC36372
0.775	Intermediate Similarity	NPC248944
0.775	Intermediate Similarity	NPC78545
0.775	Intermediate Similarity	NPC71535
0.775	Intermediate Similarity	NPC257296
0.775	Intermediate Similarity	NPC7479
0.7746	Intermediate Similarity	NPC114891
0.7722	Intermediate Similarity	NPC477817
0.7722	Intermediate Similarity	NPC31828
0.7722	Intermediate Similarity	NPC477819
0.7711	Intermediate Similarity	NPC232044
0.7711	Intermediate Similarity	NPC273290
0.7711	Intermediate Similarity	NPC290612
0.7701	Intermediate Similarity	NPC277774
0.7701	Intermediate Similarity	NPC167644
0.7701	Intermediate Similarity	NPC311246
0.7683	Intermediate Similarity	NPC85095
0.7683	Intermediate Similarity	NPC211135
0.7683	Intermediate Similarity	NPC216420
0.7671	Intermediate Similarity	NPC142712
0.7654	Intermediate Similarity	NPC469745
0.7654	Intermediate Similarity	NPC470156
0.7647	Intermediate Similarity	NPC226491
0.7647	Intermediate Similarity	NPC281004
0.7647	Intermediate Similarity	NPC477614
0.7647	Intermediate Similarity	NPC3025
0.7639	Intermediate Similarity	NPC94897
0.7632	Intermediate Similarity	NPC478103
0.7632	Intermediate Similarity	NPC195530
0.7632	Intermediate Similarity	NPC473279
0.7625	Intermediate Similarity	NPC220379
0.7619	Intermediate Similarity	NPC477283
0.7614	Intermediate Similarity	NPC477224
0.7614	Intermediate Similarity	NPC3538
0.7614	Intermediate Similarity	NPC113500
0.7614	Intermediate Similarity	NPC473503
0.7614	Intermediate Similarity	NPC309866
0.7606	Intermediate Similarity	NPC218585
0.7606	Intermediate Similarity	NPC148174
0.7606	Intermediate Similarity	NPC71460
0.76	Intermediate Similarity	NPC470830
0.76	Intermediate Similarity	NPC299948
0.76	Intermediate Similarity	NPC241085
0.7595	Intermediate Similarity	NPC212453
0.759	Intermediate Similarity	NPC50438
0.759	Intermediate Similarity	NPC255882
0.759	Intermediate Similarity	NPC227260
0.7586	Intermediate Similarity	NPC473066
0.7586	Intermediate Similarity	NPC59006
0.7586	Intermediate Similarity	NPC473830
0.7586	Intermediate Similarity	NPC204881
0.7561	Intermediate Similarity	NPC477446
0.7561	Intermediate Similarity	NPC470155
0.7561	Intermediate Similarity	NPC477447
0.7558	Intermediate Similarity	NPC20822
0.7558	Intermediate Similarity	NPC109744
0.7558	Intermediate Similarity	NPC473472
0.7558	Intermediate Similarity	NPC74258
0.7558	Intermediate Similarity	NPC102725
0.7558	Intermediate Similarity	NPC228059
0.7536	Intermediate Similarity	NPC135438
0.7534	Intermediate Similarity	NPC475943
0.7534	Intermediate Similarity	NPC190827
0.7534	Intermediate Similarity	NPC474380
0.7534	Intermediate Similarity	NPC473276
0.7534	Intermediate Similarity	NPC41577
0.7534	Intermediate Similarity	NPC243469
0.7532	Intermediate Similarity	NPC473238
0.7532	Intermediate Similarity	NPC472341
0.7531	Intermediate Similarity	NPC186588
0.7531	Intermediate Similarity	NPC472943
0.7531	Intermediate Similarity	NPC475679
0.7531	Intermediate Similarity	NPC472951
0.7529	Intermediate Similarity	NPC140446
0.7529	Intermediate Similarity	NPC43912
0.7528	Intermediate Similarity	NPC92196
0.7528	Intermediate Similarity	NPC469710
0.75	Intermediate Similarity	NPC256104
0.75	Intermediate Similarity	NPC231945
0.75	Intermediate Similarity	NPC122083
0.75	Intermediate Similarity	NPC476189

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 NPC475458 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	4422
0.2-0.3	3036
0.3-0.4	709
0.4-0.5	268
0.5-0.6	179
0.6-0.7	125
0.7-0.8	10
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8082	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6928	Phase 2
0.7733	Intermediate Similarity	NPD4787	Phase 1
0.7284	Intermediate Similarity	NPD6697	Approved
0.7284	Intermediate Similarity	NPD6118	Approved
0.7284	Intermediate Similarity	NPD6114	Approved
0.7284	Intermediate Similarity	NPD6115	Approved
0.7162	Intermediate Similarity	NPD371	Approved
0.716	Intermediate Similarity	NPD6116	Phase 1
0.7125	Intermediate Similarity	NPD3703	Phase 2
0.7111	Intermediate Similarity	NPD8171	Discontinued
0.7108	Intermediate Similarity	NPD7525	Registered
0.7037	Intermediate Similarity	NPD6117	Approved
0.6962	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3698	Phase 2
0.6923	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4245	Approved
0.6835	Remote Similarity	NPD4244	Approved
0.679	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3702	Approved
0.6706	Remote Similarity	NPD4748	Discontinued
0.6667	Remote Similarity	NPD6695	Phase 3
0.6627	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD1700	Approved
0.6596	Remote Similarity	NPD7991	Discontinued
0.6582	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD5360	Phase 3
0.6556	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6931	Approved
0.6512	Remote Similarity	NPD6930	Phase 2
0.6458	Remote Similarity	NPD4755	Approved
0.642	Remote Similarity	NPD4789	Approved
0.64	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6929	Approved
0.6386	Remote Similarity	NPD1811	Approved
0.6386	Remote Similarity	NPD1810	Approved
0.6383	Remote Similarity	NPD4202	Approved
0.6375	Remote Similarity	NPD6705	Phase 1
0.6374	Remote Similarity	NPD7750	Discontinued
0.6374	Remote Similarity	NPD7524	Approved
0.6353	Remote Similarity	NPD6932	Approved
0.6344	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6700	Approved
0.6341	Remote Similarity	NPD4758	Discontinued
0.6327	Remote Similarity	NPD4696	Approved
0.6327	Remote Similarity	NPD5286	Approved
0.6327	Remote Similarity	NPD5285	Approved
0.6327	Remote Similarity	NPD4700	Approved
0.6324	Remote Similarity	NPD385	Approved
0.6324	Remote Similarity	NPD384	Approved
0.631	Remote Similarity	NPD7339	Approved
0.631	Remote Similarity	NPD6942	Approved
0.6279	Remote Similarity	NPD3671	Phase 1
0.6277	Remote Similarity	NPD6702	Approved
0.6277	Remote Similarity	NPD6703	Approved
0.6224	Remote Similarity	NPD7638	Approved
0.622	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7645	Phase 2
0.6207	Remote Similarity	NPD6683	Phase 2
0.62	Remote Similarity	NPD5225	Approved
0.62	Remote Similarity	NPD5226	Approved
0.62	Remote Similarity	NPD5224	Approved
0.62	Remote Similarity	NPD4633	Approved
0.62	Remote Similarity	NPD5211	Phase 2
0.619	Remote Similarity	NPD6926	Approved
0.619	Remote Similarity	NPD6924	Approved
0.6176	Remote Similarity	NPD6402	Approved
0.6176	Remote Similarity	NPD7128	Approved
0.6176	Remote Similarity	NPD5739	Approved
0.6176	Remote Similarity	NPD388	Approved
0.6176	Remote Similarity	NPD6675	Approved
0.6176	Remote Similarity	NPD386	Approved
0.6163	Remote Similarity	NPD5776	Phase 2
0.6163	Remote Similarity	NPD6925	Approved
0.6162	Remote Similarity	NPD7640	Approved
0.6162	Remote Similarity	NPD7639	Approved
0.6154	Remote Similarity	NPD6893	Approved
0.6154	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD7328	Approved
0.6147	Remote Similarity	NPD7327	Approved
0.6145	Remote Similarity	NPD5777	Approved
0.6145	Remote Similarity	NPD4243	Approved
0.6139	Remote Similarity	NPD5174	Approved
0.6139	Remote Similarity	NPD5175	Approved
0.6136	Remote Similarity	NPD7514	Phase 3
0.6117	Remote Similarity	NPD5697	Approved
0.6117	Remote Similarity	NPD5701	Approved
0.6111	Remote Similarity	NPD4788	Approved
0.6105	Remote Similarity	NPD8034	Phase 2
0.6105	Remote Similarity	NPD8035	Phase 2
0.6105	Remote Similarity	NPD7087	Discontinued
0.61	Remote Similarity	NPD5223	Approved
0.61	Remote Similarity	NPD4159	Approved
0.6095	Remote Similarity	NPD4634	Approved
0.6092	Remote Similarity	NPD5364	Discontinued
0.6092	Remote Similarity	NPD7145	Approved
0.6091	Remote Similarity	NPD7516	Approved
0.6087	Remote Similarity	NPD8308	Discontinued
0.6078	Remote Similarity	NPD5141	Approved
0.6075	Remote Similarity	NPD4632	Approved
0.6064	Remote Similarity	NPD4753	Phase 2
0.6058	Remote Similarity	NPD7320	Approved
0.6058	Remote Similarity	NPD6899	Approved
0.6058	Remote Similarity	NPD6881	Approved
0.6047	Remote Similarity	NPD6933	Approved
0.604	Remote Similarity	NPD7632	Discontinued
0.6024	Remote Similarity	NPD2254	Approved
0.6024	Remote Similarity	NPD2686	Approved
0.6024	Remote Similarity	NPD2687	Approved
0.6019	Remote Similarity	NPD4768	Approved
0.6019	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD6014	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD4784	Approved
0.6	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD4785	Approved
0.6	Remote Similarity	NPD6012	Approved
0.6	Remote Similarity	NPD6373	Approved
0.5982	Remote Similarity	NPD8335	Approved
0.5982	Remote Similarity	NPD8380	Approved
0.5982	Remote Similarity	NPD8378	Approved
0.5982	Remote Similarity	NPD8379	Approved
0.5982	Remote Similarity	NPD8296	Approved
0.5982	Remote Similarity	NPD8033	Approved
0.598	Remote Similarity	NPD4754	Approved
0.5955	Remote Similarity	NPD7332	Phase 2
0.5955	Remote Similarity	NPD7509	Discontinued
0.5952	Remote Similarity	NPD6081	Approved
0.5943	Remote Similarity	NPD7102	Approved
0.5943	Remote Similarity	NPD6883	Approved
0.5943	Remote Similarity	NPD7290	Approved
0.593	Remote Similarity	NPD4190	Phase 3
0.593	Remote Similarity	NPD5275	Approved
0.5926	Remote Similarity	NPD4224	Phase 2
0.5914	Remote Similarity	NPD3618	Phase 1
0.5909	Remote Similarity	NPD6009	Approved
0.5905	Remote Similarity	NPD6011	Approved
0.5905	Remote Similarity	NPD4729	Approved
0.5905	Remote Similarity	NPD4730	Approved
0.5905	Remote Similarity	NPD5128	Approved
0.5895	Remote Similarity	NPD5328	Approved
0.5893	Remote Similarity	NPD8294	Approved
0.5893	Remote Similarity	NPD6319	Approved
0.5893	Remote Similarity	NPD6059	Approved
0.5893	Remote Similarity	NPD6054	Approved
0.5893	Remote Similarity	NPD8377	Approved
0.5889	Remote Similarity	NPD6898	Phase 1
0.5889	Remote Similarity	NPD6902	Approved
0.5888	Remote Similarity	NPD8130	Phase 1
0.5888	Remote Similarity	NPD6847	Approved
0.5888	Remote Similarity	NPD6617	Approved
0.5888	Remote Similarity	NPD6649	Approved
0.5888	Remote Similarity	NPD6650	Approved
0.5888	Remote Similarity	NPD6869	Approved
0.587	Remote Similarity	NPD4786	Approved
0.587	Remote Similarity	NPD3666	Approved
0.587	Remote Similarity	NPD3133	Approved
0.587	Remote Similarity	NPD3665	Phase 1
0.5865	Remote Similarity	NPD6008	Approved
0.5849	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD4195	Approved
0.5842	Remote Similarity	NPD8418	Phase 2
0.5841	Remote Similarity	NPD6016	Approved
0.5841	Remote Similarity	NPD6015	Approved
0.5833	Remote Similarity	NPD8297	Approved
0.5833	Remote Similarity	NPD6882	Approved
0.5824	Remote Similarity	NPD3667	Approved
0.581	Remote Similarity	NPD6412	Phase 2
0.58	Remote Similarity	NPD6084	Phase 2
0.58	Remote Similarity	NPD6083	Phase 2
0.5794	Remote Similarity	NPD5247	Approved
0.5794	Remote Similarity	NPD5248	Approved
0.5794	Remote Similarity	NPD5250	Approved
0.5794	Remote Similarity	NPD5251	Approved
0.5794	Remote Similarity	NPD5249	Phase 3
0.5789	Remote Similarity	NPD5988	Approved
0.5789	Remote Similarity	NPD6370	Approved
0.5789	Remote Similarity	NPD586	Phase 1
0.578	Remote Similarity	NPD8133	Approved
0.5773	Remote Similarity	NPD6079	Approved
0.5765	Remote Similarity	NPD7150	Approved
0.5765	Remote Similarity	NPD7152	Approved
0.5765	Remote Similarity	NPD7151	Approved
0.5761	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD3669	Approved
0.5758	Remote Similarity	NPD4629	Approved
0.5758	Remote Similarity	NPD5210	Approved
0.5755	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD5217	Approved
0.5741	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD5215	Approved
0.5741	Remote Similarity	NPD5216	Approved
0.5714	Remote Similarity	NPD6922	Approved
0.5714	Remote Similarity	NPD6923	Approved
0.5714	Remote Similarity	NPD6399	Phase 3
0.5702	Remote Similarity	NPD5983	Phase 2

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