NPASS Compound

Structure

CID283087 OpenBabel06191716092D 23 25 0 0 1 0 0 0 0 0999 V2000 -0.7326 2.4022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7130 1.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1704 2.4539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0451 1.9485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3355 -1.0107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9347 -1.4385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0036 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0038 0.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1698 -0.4822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5018 1.4442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8334 1.4448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6681 0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3359 0.9626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 0.9633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 1.4445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8336 -0.4816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1702 1.4439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3357 -0.0007 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8340 2.4478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8335 -1.4848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8338 -0.4812 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 23 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 10 13 2 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 17 18 1 0 0 0 0 17 22 2 0 0 0 0 18 23 1 0 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.19
Volume:	341.995
LogP:	5.452
LogD:	4.237
LogS:	-4.596
# Rotatable Bonds:	2
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.755
Synthetic Accessibility Score:	4.008
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.901
MDCK Permeability:	2.0690664314315654e-05
Pgp-inhibitor:	0.269
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.097
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059
Plasma Protein Binding (PPB):	98.08330535888672%
Volume Distribution (VD):	2.404
Pgp-substrate:	4.493261337280273%

ADMET: Metabolism

CYP1A2-inhibitor:	0.657
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.387
CYP2C19-substrate:	0.862
CYP2C9-inhibitor:	0.567
CYP2C9-substrate:	0.847
CYP2D6-inhibitor:	0.245
CYP2D6-substrate:	0.219
CYP3A4-inhibitor:	0.52
CYP3A4-substrate:	0.775

ADMET: Excretion

Clearance (CL):	8.931
Half-life (T1/2):	0.173

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.458
Drug-inuced Liver Injury (DILI):	0.221
AMES Toxicity:	0.147
Rat Oral Acute Toxicity:	0.66
Maximum Recommended Daily Dose:	0.367
Skin Sensitization:	0.683
Carcinogencity:	0.701
Eye Corrosion:	0.004
Eye Irritation:	0.552
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC283087

Natural Product ID:	NPC283087
*Common Name:**	Taiwaniaquinone H
IUPAC Name:	(4bS)-3-methoxy-4b,8,8-trimethyl-2-propan-2-yl-6,7-dihydro-5H-fluorene-1,4-dione
Synonyms:	Taiwaniaquinone H
Standard InCHIKey:	LEXZEULYIQDNCX-FQEVSTJZSA-N
Standard InCHI:	InChI=1S/C20H26O3/c1-11(2)14-16(21)12-10-13-19(3,4)8-7-9-20(13,5)15(12)17(22)18(14)23-6/h10-11H,7-9H2,1-6H3/t20-/m0/s1
SMILES:	CC(C)C1=C(C(=O)C2=C(C=C3C(C)(C)CCC[C@]23C)C1=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077114
PubChem CID:	44597340
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
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	twig	n.a.	PMID[22474975]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31347365]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9014350]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	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
EC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	EC50	>	10000.0	nM	PMID[511243]

☑ 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 NPC283087 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	183
0.1-0.2	1232
0.2-0.3	5972
0.3-0.4	16472
0.4-0.5	11068
0.5-0.6	5743
0.6-0.7	1854
0.7-0.8	160
0.8-0.85	10
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8816	High Similarity	NPC23778
0.8481	Intermediate Similarity	NPC474085
0.8272	Intermediate Similarity	NPC8091
0.8267	Intermediate Similarity	NPC474539
0.8077	Intermediate Similarity	NPC110725
0.8072	Intermediate Similarity	NPC6185
0.8072	Intermediate Similarity	NPC241512
0.8072	Intermediate Similarity	NPC132228
0.8072	Intermediate Similarity	NPC263997
0.8072	Intermediate Similarity	NPC8518
0.8072	Intermediate Similarity	NPC133652
0.8052	Intermediate Similarity	NPC147438
0.8025	Intermediate Similarity	NPC225515
0.7857	Intermediate Similarity	NPC32037
0.7831	Intermediate Similarity	NPC288281
0.7808	Intermediate Similarity	NPC474400
0.7808	Intermediate Similarity	NPC34622
0.7791	Intermediate Similarity	NPC53454
0.7778	Intermediate Similarity	NPC27817
0.7722	Intermediate Similarity	NPC175079
0.7703	Intermediate Similarity	NPC98897
0.7701	Intermediate Similarity	NPC280833
0.7683	Intermediate Similarity	NPC108955
0.7671	Intermediate Similarity	NPC57463
0.7671	Intermediate Similarity	NPC151728
0.7654	Intermediate Similarity	NPC469996
0.7654	Intermediate Similarity	NPC189485
0.7654	Intermediate Similarity	NPC478246
0.7654	Intermediate Similarity	NPC478247
0.7647	Intermediate Similarity	NPC474680
0.7647	Intermediate Similarity	NPC90287
0.7625	Intermediate Similarity	NPC92080
0.7625	Intermediate Similarity	NPC26504
0.7614	Intermediate Similarity	NPC475823
0.7614	Intermediate Similarity	NPC474209
0.7614	Intermediate Similarity	NPC223093
0.76	Intermediate Similarity	NPC16119
0.759	Intermediate Similarity	NPC121984
0.759	Intermediate Similarity	NPC99308
0.759	Intermediate Similarity	NPC55869
0.7561	Intermediate Similarity	NPC476177
0.7558	Intermediate Similarity	NPC203795
0.7531	Intermediate Similarity	NPC472300
0.7528	Intermediate Similarity	NPC174167
0.7528	Intermediate Similarity	NPC470036
0.75	Intermediate Similarity	NPC474619
0.75	Intermediate Similarity	NPC243272
0.75	Intermediate Similarity	NPC103486
0.7473	Intermediate Similarity	NPC295347
0.7444	Intermediate Similarity	NPC263780
0.7442	Intermediate Similarity	NPC470177
0.7439	Intermediate Similarity	NPC30321
0.7412	Intermediate Similarity	NPC105803
0.7407	Intermediate Similarity	NPC40353
0.7403	Intermediate Similarity	NPC263382
0.7403	Intermediate Similarity	NPC146376
0.7403	Intermediate Similarity	NPC134385
0.7403	Intermediate Similarity	NPC125578
0.7386	Intermediate Similarity	NPC472302
0.7381	Intermediate Similarity	NPC475833
0.7381	Intermediate Similarity	NPC149237
0.7349	Intermediate Similarity	NPC475681
0.7333	Intermediate Similarity	NPC166110
0.7326	Intermediate Similarity	NPC237712
0.7326	Intermediate Similarity	NPC469569
0.7312	Intermediate Similarity	NPC208094
0.7308	Intermediate Similarity	NPC94488
0.7308	Intermediate Similarity	NPC474060
0.7308	Intermediate Similarity	NPC262673
0.7303	Intermediate Similarity	NPC68148
0.7303	Intermediate Similarity	NPC112454
0.7303	Intermediate Similarity	NPC474918
0.7303	Intermediate Similarity	NPC65615
0.7294	Intermediate Similarity	NPC327969
0.7294	Intermediate Similarity	NPC321289
0.7284	Intermediate Similarity	NPC473171
0.7283	Intermediate Similarity	NPC280725
0.7283	Intermediate Similarity	NPC777
0.7283	Intermediate Similarity	NPC31021
0.7273	Intermediate Similarity	NPC38885
0.7273	Intermediate Similarity	NPC181327
0.7262	Intermediate Similarity	NPC2482
0.7262	Intermediate Similarity	NPC287063
0.726	Intermediate Similarity	NPC473494
0.7253	Intermediate Similarity	NPC248193
0.7253	Intermediate Similarity	NPC211230
0.7229	Intermediate Similarity	NPC476808
0.7222	Intermediate Similarity	NPC129913
0.7215	Intermediate Similarity	NPC94743
0.7215	Intermediate Similarity	NPC291062
0.7209	Intermediate Similarity	NPC53733
0.7195	Intermediate Similarity	NPC470525
0.7195	Intermediate Similarity	NPC263582
0.7195	Intermediate Similarity	NPC1254
0.7195	Intermediate Similarity	NPC180886
0.7195	Intermediate Similarity	NPC899
0.7179	Intermediate Similarity	NPC155198
0.7179	Intermediate Similarity	NPC310992
0.7176	Intermediate Similarity	NPC474955
0.7176	Intermediate Similarity	NPC475863
0.7176	Intermediate Similarity	NPC474353
0.7176	Intermediate Similarity	NPC478262
0.7176	Intermediate Similarity	NPC475665
0.7176	Intermediate Similarity	NPC470034
0.7174	Intermediate Similarity	NPC474882
0.7174	Intermediate Similarity	NPC474328
0.7162	Intermediate Similarity	NPC127582
0.716	Intermediate Similarity	NPC264178
0.716	Intermediate Similarity	NPC306928
0.7159	Intermediate Similarity	NPC94666
0.7159	Intermediate Similarity	NPC327115
0.7143	Intermediate Similarity	NPC474113
0.7143	Intermediate Similarity	NPC192329
0.7143	Intermediate Similarity	NPC26865
0.7143	Intermediate Similarity	NPC150646
0.7126	Intermediate Similarity	NPC144258
0.7126	Intermediate Similarity	NPC474359
0.7126	Intermediate Similarity	NPC320801
0.7125	Intermediate Similarity	NPC5734
0.7111	Intermediate Similarity	NPC284561
0.7111	Intermediate Similarity	NPC305039
0.7111	Intermediate Similarity	NPC95364
0.7111	Intermediate Similarity	NPC142159
0.7111	Intermediate Similarity	NPC118011
0.7111	Intermediate Similarity	NPC36668
0.7108	Intermediate Similarity	NPC165711
0.7093	Intermediate Similarity	NPC268122
0.7093	Intermediate Similarity	NPC100297
0.7089	Intermediate Similarity	NPC256846
0.7089	Intermediate Similarity	NPC139397
0.7079	Intermediate Similarity	NPC477228
0.7079	Intermediate Similarity	NPC136548
0.7073	Intermediate Similarity	NPC475771
0.7073	Intermediate Similarity	NPC469678
0.7073	Intermediate Similarity	NPC469669
0.7065	Intermediate Similarity	NPC134826
0.7059	Intermediate Similarity	NPC304795
0.7059	Intermediate Similarity	NPC472478
0.7059	Intermediate Similarity	NPC18955
0.7045	Intermediate Similarity	NPC300985
0.7045	Intermediate Similarity	NPC478245
0.7045	Intermediate Similarity	NPC33881
0.7045	Intermediate Similarity	NPC323765
0.7045	Intermediate Similarity	NPC470048
0.7045	Intermediate Similarity	NPC189311
0.7045	Intermediate Similarity	NPC469948
0.7037	Intermediate Similarity	NPC247586
0.7033	Intermediate Similarity	NPC220454
0.7033	Intermediate Similarity	NPC213636
0.7033	Intermediate Similarity	NPC253177
0.7033	Intermediate Similarity	NPC280592
0.7033	Intermediate Similarity	NPC212679
0.7033	Intermediate Similarity	NPC469595
0.7024	Intermediate Similarity	NPC99182
0.7024	Intermediate Similarity	NPC471220
0.7024	Intermediate Similarity	NPC471409
0.7024	Intermediate Similarity	NPC62336
0.7024	Intermediate Similarity	NPC35574
0.7024	Intermediate Similarity	NPC4827
0.7024	Intermediate Similarity	NPC475994
0.7024	Intermediate Similarity	NPC275494
0.7013	Intermediate Similarity	NPC251118
0.7011	Intermediate Similarity	NPC258985
0.7011	Intermediate Similarity	NPC193198
0.7011	Intermediate Similarity	NPC309309
0.7011	Intermediate Similarity	NPC291999
0.7011	Intermediate Similarity	NPC470165
0.7011	Intermediate Similarity	NPC102197
0.7011	Intermediate Similarity	NPC118423
0.7	Intermediate Similarity	NPC478260
0.7	Intermediate Similarity	NPC478261
0.7	Intermediate Similarity	NPC307298
0.7	Intermediate Similarity	NPC265782
0.7	Intermediate Similarity	NPC185059
0.7	Intermediate Similarity	NPC251929
0.7	Intermediate Similarity	NPC2634
0.7	Intermediate Similarity	NPC260040
0.7	Intermediate Similarity	NPC475001
0.7	Intermediate Similarity	NPC307176
0.7	Intermediate Similarity	NPC478259
0.7	Intermediate Similarity	NPC173321
0.6989	Remote Similarity	NPC473162
0.6988	Remote Similarity	NPC469796
0.6988	Remote Similarity	NPC473223
0.6988	Remote Similarity	NPC469793
0.6977	Remote Similarity	NPC472684
0.6977	Remote Similarity	NPC136150
0.6977	Remote Similarity	NPC477372
0.6977	Remote Similarity	NPC189237
0.6977	Remote Similarity	NPC44963
0.6977	Remote Similarity	NPC116797
0.6974	Remote Similarity	NPC477830
0.6974	Remote Similarity	NPC53109
0.6974	Remote Similarity	NPC143168
0.6974	Remote Similarity	NPC167256
0.6966	Remote Similarity	NPC195640
0.6966	Remote Similarity	NPC474732
0.6966	Remote Similarity	NPC51014
0.6966	Remote Similarity	NPC474733
0.6966	Remote Similarity	NPC470345

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 NPC283087 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1522
0.2-0.3	4212
0.3-0.4	2351
0.4-0.5	564
0.5-0.6	222
0.6-0.7	93
0.7-0.8	14
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
0.7683	Intermediate Similarity	NPD4695	Discontinued
0.76	Intermediate Similarity	NPD6108	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD5279	Phase 3
0.7439	Intermediate Similarity	NPD3617	Approved
0.7416	Intermediate Similarity	NPD5692	Phase 3
0.7386	Intermediate Similarity	NPD5737	Approved
0.7386	Intermediate Similarity	NPD6672	Approved
0.7356	Intermediate Similarity	NPD4694	Approved
0.7356	Intermediate Similarity	NPD5280	Approved
0.7342	Intermediate Similarity	NPD5276	Approved
0.7333	Intermediate Similarity	NPD5694	Approved
0.7333	Intermediate Similarity	NPD6050	Approved
0.7303	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4687	Approved
0.716	Intermediate Similarity	NPD5733	Approved
0.716	Intermediate Similarity	NPD4058	Approved
0.7143	Intermediate Similarity	NPD3704	Approved
0.7126	Intermediate Similarity	NPD4197	Approved
0.7111	Intermediate Similarity	NPD6904	Approved
0.7111	Intermediate Similarity	NPD6080	Approved
0.7111	Intermediate Similarity	NPD6673	Approved
0.7108	Intermediate Similarity	NPD4756	Discovery
0.7097	Intermediate Similarity	NPD5654	Approved
0.7089	Intermediate Similarity	NPD4137	Phase 3
0.7045	Intermediate Similarity	NPD5329	Approved
0.7	Intermediate Similarity	NPD4691	Approved
0.7	Intermediate Similarity	NPD4747	Approved
0.6974	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7334	Approved
0.6966	Remote Similarity	NPD7146	Approved
0.6966	Remote Similarity	NPD5690	Phase 2
0.6966	Remote Similarity	NPD6684	Approved
0.6966	Remote Similarity	NPD5330	Approved
0.6966	Remote Similarity	NPD6098	Approved
0.6966	Remote Similarity	NPD7521	Approved
0.6966	Remote Similarity	NPD6409	Approved
0.6957	Remote Similarity	NPD5693	Phase 1
0.6947	Remote Similarity	NPD5959	Approved
0.6932	Remote Similarity	NPD3666	Approved
0.6932	Remote Similarity	NPD3133	Approved
0.6932	Remote Similarity	NPD3665	Phase 1
0.6923	Remote Similarity	NPD4753	Phase 2
0.6915	Remote Similarity	NPD5695	Phase 3
0.6897	Remote Similarity	NPD4223	Phase 3
0.6897	Remote Similarity	NPD4221	Approved
0.6897	Remote Similarity	NPD3667	Approved
0.6882	Remote Similarity	NPD5133	Approved
0.686	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD1696	Phase 3
0.6848	Remote Similarity	NPD5207	Approved
0.6813	Remote Similarity	NPD6903	Approved
0.6813	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5282	Discontinued
0.6778	Remote Similarity	NPD4623	Approved
0.6778	Remote Similarity	NPD3618	Phase 1
0.6778	Remote Similarity	NPD4519	Discontinued
0.6771	Remote Similarity	NPD6084	Phase 2
0.6771	Remote Similarity	NPD6083	Phase 2
0.6742	Remote Similarity	NPD4786	Approved
0.6742	Remote Similarity	NPD3668	Phase 3
0.6709	Remote Similarity	NPD7331	Phase 2
0.6705	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD4096	Approved
0.663	Remote Similarity	NPD4518	Approved
0.663	Remote Similarity	NPD5208	Approved
0.6596	Remote Similarity	NPD5281	Approved
0.6596	Remote Similarity	NPD5284	Approved
0.6593	Remote Similarity	NPD4690	Approved
0.6593	Remote Similarity	NPD4688	Approved
0.6593	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5205	Approved
0.6593	Remote Similarity	NPD4689	Approved
0.6593	Remote Similarity	NPD4693	Phase 3
0.6593	Remote Similarity	NPD4138	Approved
0.6582	Remote Similarity	NPD7341	Phase 2
0.6562	Remote Similarity	NPD5210	Approved
0.6562	Remote Similarity	NPD4629	Approved
0.6559	Remote Similarity	NPD5328	Approved
0.6543	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD8779	Phase 3
0.6522	Remote Similarity	NPD3573	Approved
0.6495	Remote Similarity	NPD5222	Approved
0.6495	Remote Similarity	NPD5221	Approved
0.6495	Remote Similarity	NPD4697	Phase 3
0.6495	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8039	Approved
0.6444	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4755	Approved
0.6429	Remote Similarity	NPD5173	Approved
0.6421	Remote Similarity	NPD6079	Approved
0.6392	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4202	Approved
0.6354	Remote Similarity	NPD6399	Phase 3
0.6311	Remote Similarity	NPD5739	Approved
0.6311	Remote Similarity	NPD6402	Approved
0.6311	Remote Similarity	NPD6675	Approved
0.6311	Remote Similarity	NPD7128	Approved
0.63	Remote Similarity	NPD5286	Approved
0.63	Remote Similarity	NPD5285	Approved
0.63	Remote Similarity	NPD4700	Approved
0.63	Remote Similarity	NPD4696	Approved
0.6289	Remote Similarity	NPD7748	Approved
0.6289	Remote Similarity	NPD6001	Approved
0.6289	Remote Similarity	NPD7900	Approved
0.6289	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7515	Phase 2
0.625	Remote Similarity	NPD5697	Approved
0.625	Remote Similarity	NPD5701	Approved
0.6238	Remote Similarity	NPD5223	Approved
0.6234	Remote Similarity	NPD287	Approved
0.6222	Remote Similarity	NPD4692	Approved
0.6222	Remote Similarity	NPD4139	Approved
0.619	Remote Similarity	NPD6011	Approved
0.619	Remote Similarity	NPD7320	Approved
0.619	Remote Similarity	NPD6881	Approved
0.619	Remote Similarity	NPD6899	Approved
0.618	Remote Similarity	NPD4195	Approved
0.6176	Remote Similarity	NPD4633	Approved
0.6176	Remote Similarity	NPD5225	Approved
0.6176	Remote Similarity	NPD5224	Approved
0.6176	Remote Similarity	NPD5211	Phase 2
0.6176	Remote Similarity	NPD5226	Approved
0.6162	Remote Similarity	NPD7732	Phase 3
0.6154	Remote Similarity	NPD5209	Approved
0.6132	Remote Similarity	NPD6014	Approved
0.6132	Remote Similarity	NPD6012	Approved
0.6132	Remote Similarity	NPD6372	Approved
0.6132	Remote Similarity	NPD6013	Approved
0.6132	Remote Similarity	NPD6373	Approved
0.6117	Remote Similarity	NPD5174	Approved
0.6117	Remote Similarity	NPD4754	Approved
0.6117	Remote Similarity	NPD5175	Approved
0.61	Remote Similarity	NPD7902	Approved
0.6095	Remote Similarity	NPD6614	Approved
0.6087	Remote Similarity	NPD4788	Approved
0.6087	Remote Similarity	NPD7154	Phase 3
0.6082	Remote Similarity	NPD6411	Approved
0.6075	Remote Similarity	NPD7290	Approved
0.6075	Remote Similarity	NPD7102	Approved
0.6075	Remote Similarity	NPD6883	Approved
0.6058	Remote Similarity	NPD5141	Approved
0.6044	Remote Similarity	NPD8028	Phase 2
0.6019	Remote Similarity	NPD6650	Approved
0.6019	Remote Similarity	NPD8130	Phase 1
0.6019	Remote Similarity	NPD6847	Approved
0.6019	Remote Similarity	NPD5091	Approved
0.6019	Remote Similarity	NPD6649	Approved
0.6019	Remote Similarity	NPD6869	Approved
0.6019	Remote Similarity	NPD6617	Approved
0.6019	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD4768	Approved
0.5978	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD6926	Approved
0.5977	Remote Similarity	NPD6924	Approved
0.5963	Remote Similarity	NPD6882	Approved
0.5963	Remote Similarity	NPD8297	Approved
0.5914	Remote Similarity	NPD6110	Phase 1
0.5888	Remote Similarity	NPD4730	Approved
0.5888	Remote Similarity	NPD5168	Approved
0.5888	Remote Similarity	NPD4729	Approved
0.5888	Remote Similarity	NPD5128	Approved
0.5882	Remote Similarity	NPD6922	Approved
0.5882	Remote Similarity	NPD6923	Approved
0.5876	Remote Similarity	NPD6101	Approved
0.5876	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD6933	Approved
0.5843	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD7614	Phase 1
0.5825	Remote Similarity	NPD6404	Discontinued
0.5816	Remote Similarity	NPD5785	Approved
0.5814	Remote Similarity	NPD7143	Approved
0.5814	Remote Similarity	NPD7144	Approved
0.581	Remote Similarity	NPD6052	Approved
0.5804	Remote Similarity	NPD6868	Approved
0.5804	Remote Similarity	NPD6274	Approved
0.58	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6412	Phase 2
0.578	Remote Similarity	NPD5250	Approved
0.578	Remote Similarity	NPD5135	Approved
0.578	Remote Similarity	NPD5249	Phase 3
0.578	Remote Similarity	NPD5248	Approved
0.578	Remote Similarity	NPD5247	Approved
0.578	Remote Similarity	NPD2067	Discontinued
0.578	Remote Similarity	NPD5169	Approved
0.578	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.578	Remote Similarity	NPD4634	Approved
0.578	Remote Similarity	NPD5251	Approved
0.5776	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD6858	Approved
0.5766	Remote Similarity	NPD4632	Approved
0.5766	Remote Similarity	NPD7094	Approved
0.5761	Remote Similarity	NPD7509	Discontinued
0.5752	Remote Similarity	NPD6009	Approved
0.5752	Remote Similarity	NPD6317	Approved
0.5747	Remote Similarity	NPD7151	Approved
0.5747	Remote Similarity	NPD7150	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