NPASS Compound

Structure

CID276815 OpenBabel06191716082D 24 26 0 0 1 0 0 0 0 0999 V2000 4.2691 -2.4026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9475 -0.8796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8346 -2.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7091 -1.9489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 1.0099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5607 1.3597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6677 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6678 -0.9628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1686 -1.4453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3351 -0.9638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6675 -0.9635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6677 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5014 -1.4450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8338 -1.4447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5018 0.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3353 -0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 -0.9632 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8344 -1.4443 0.0000 C 0 0 0 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 2.5014 -2.4481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8337 -2.4478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5019 1.4840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1690 0.4804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 24 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 11 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 15 22 2 0 0 0 0 16 17 2 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 6 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	353.422
LogP:	4.998
LogD:	3.791
LogS:	-4.588
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.782
Synthetic Accessibility Score:	4.039
Fsp3:	0.65
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:	-4.794
MDCK Permeability:	1.9983523088740185e-05
Pgp-inhibitor:	0.422
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.044
20% Bioavailability (F20%):	0.772
30% Bioavailability (F30%):	0.778

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.214
Plasma Protein Binding (PPB):	99.10493469238281%
Volume Distribution (VD):	2.341
Pgp-substrate:	2.655592441558838%

ADMET: Metabolism

CYP1A2-inhibitor:	0.526
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.475
CYP2C19-substrate:	0.85
CYP2C9-inhibitor:	0.63
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.486
CYP2D6-substrate:	0.342
CYP3A4-inhibitor:	0.393
CYP3A4-substrate:	0.474

ADMET: Excretion

Clearance (CL):	1.862
Half-life (T1/2):	0.058

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.181
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.228
Maximum Recommended Daily Dose:	0.115
Skin Sensitization:	0.834
Carcinogencity:	0.051
Eye Corrosion:	0.003
Eye Irritation:	0.788
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC276815

Natural Product ID:	NPC276815
*Common Name:**	Taiwaniaquinol B
IUPAC Name:	(4aS,9aR)-5,8-dihydroxy-6-methoxy-1,1,4a-trimethyl-7-propan-2-yl-2,3,4,9a-tetrahydrofluoren-9-one
Synonyms:
Standard InCHIKey:	PZLPUCMOBKVMOI-UYAOXDASSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-10(2)11-14(21)12-13(16(23)17(11)24-6)20(5)9-7-8-19(3,4)18(20)15(12)22/h10,18,21,23H,7-9H2,1-6H3/t18-,20-/m1/s1
SMILES:	COc1c(C(C)C)c(O)c2c(c1O)[C@@]1(C)CCCC([C@H]1C2=O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087912
PubChem CID:	11688549
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[559020]

☑ 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 NPC276815 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	427
0.1-0.2	1893
0.2-0.3	3827
0.3-0.4	9502
0.4-0.5	9552
0.5-0.6	4518
0.6-0.7	6484
0.7-0.8	5784
0.8-0.85	624
0.85-0.9	63
0.9-0.95	18
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC25850
0.9933	High Similarity	NPC283301
0.96	High Similarity	NPC273248
0.9533	High Similarity	NPC161778
0.9276	High Similarity	NPC218628
0.9272	High Similarity	NPC50269
0.9177	High Similarity	NPC102372
0.9114	High Similarity	NPC208120
0.9114	High Similarity	NPC173587
0.9062	High Similarity	NPC232936
0.9057	High Similarity	NPC146584
0.9057	High Similarity	NPC21016
0.9006	High Similarity	NPC213416
0.8994	High Similarity	NPC475055
0.8994	High Similarity	NPC29055
0.891	High Similarity	NPC472048
0.8805	High Similarity	NPC84571
0.8805	High Similarity	NPC155302
0.8805	High Similarity	NPC161947
0.88	High Similarity	NPC92079
0.8797	High Similarity	NPC179732
0.8758	High Similarity	NPC236132
0.8758	High Similarity	NPC220313
0.8758	High Similarity	NPC270837
0.875	High Similarity	NPC311740
0.875	High Similarity	NPC87431
0.8742	High Similarity	NPC45846
0.8734	High Similarity	NPC48105
0.8734	High Similarity	NPC470762
0.8734	High Similarity	NPC474167
0.8696	High Similarity	NPC294965
0.8696	High Similarity	NPC470694
0.8688	High Similarity	NPC228785
0.8688	High Similarity	NPC56085
0.8688	High Similarity	NPC14353
0.8679	High Similarity	NPC37543
0.8679	High Similarity	NPC199463
0.8642	High Similarity	NPC319200
0.8642	High Similarity	NPC187491
0.8634	High Similarity	NPC32694
0.8634	High Similarity	NPC61010
0.8634	High Similarity	NPC40491
0.8634	High Similarity	NPC278052
0.8634	High Similarity	NPC66288
0.8634	High Similarity	NPC65746
0.8625	High Similarity	NPC100123
0.8616	High Similarity	NPC14561
0.8616	High Similarity	NPC5379
0.8616	High Similarity	NPC77807
0.8608	High Similarity	NPC477048
0.8608	High Similarity	NPC477047
0.8589	High Similarity	NPC473286
0.8589	High Similarity	NPC326520
0.8589	High Similarity	NPC25361
0.8581	High Similarity	NPC251188
0.858	High Similarity	NPC215612
0.8571	High Similarity	NPC119224
0.8571	High Similarity	NPC235018
0.8571	High Similarity	NPC45146
0.8571	High Similarity	NPC80375
0.8571	High Similarity	NPC320359
0.8562	High Similarity	NPC178976
0.8562	High Similarity	NPC241904
0.8562	High Similarity	NPC217677
0.8562	High Similarity	NPC300727
0.8562	High Similarity	NPC165977
0.8553	High Similarity	NPC130589
0.8553	High Similarity	NPC134287
0.8537	High Similarity	NPC170245
0.8537	High Similarity	NPC37870
0.8535	High Similarity	NPC472279
0.8528	High Similarity	NPC7483
0.8528	High Similarity	NPC236521
0.8528	High Similarity	NPC152659
0.8528	High Similarity	NPC197168
0.8528	High Similarity	NPC476822
0.8528	High Similarity	NPC248638
0.8526	High Similarity	NPC131451
0.8526	High Similarity	NPC15329
0.8519	High Similarity	NPC472275
0.8509	High Similarity	NPC235448
0.8509	High Similarity	NPC476242
0.85	High Similarity	NPC142339
0.85	High Similarity	NPC274730
0.8491	Intermediate Similarity	NPC107109
0.8491	Intermediate Similarity	NPC93552
0.8485	Intermediate Similarity	NPC126204
0.8476	Intermediate Similarity	NPC239752
0.8476	Intermediate Similarity	NPC26386
0.8476	Intermediate Similarity	NPC472450
0.8476	Intermediate Similarity	NPC275780
0.8471	Intermediate Similarity	NPC92722
0.8471	Intermediate Similarity	NPC303989
0.8471	Intermediate Similarity	NPC102003
0.8466	Intermediate Similarity	NPC25152
0.8462	Intermediate Similarity	NPC77179
0.8462	Intermediate Similarity	NPC23553
0.8457	Intermediate Similarity	NPC475886
0.8457	Intermediate Similarity	NPC474287
0.8447	Intermediate Similarity	NPC236796
0.8447	Intermediate Similarity	NPC78225
0.8447	Intermediate Similarity	NPC469584
0.8447	Intermediate Similarity	NPC302258
0.8447	Intermediate Similarity	NPC180011
0.8447	Intermediate Similarity	NPC79053
0.8447	Intermediate Similarity	NPC36852
0.8447	Intermediate Similarity	NPC78103
0.8447	Intermediate Similarity	NPC262286
0.8447	Intermediate Similarity	NPC219867
0.8443	Intermediate Similarity	NPC158226
0.8438	Intermediate Similarity	NPC234485
0.8438	Intermediate Similarity	NPC39184
0.8434	Intermediate Similarity	NPC165979
0.8434	Intermediate Similarity	NPC475805
0.8434	Intermediate Similarity	NPC163130
0.8434	Intermediate Similarity	NPC476637
0.8424	Intermediate Similarity	NPC39091
0.8424	Intermediate Similarity	NPC472452
0.8421	Intermediate Similarity	NPC240508
0.8421	Intermediate Similarity	NPC228209
0.8421	Intermediate Similarity	NPC246153
0.8418	Intermediate Similarity	NPC103509
0.8415	Intermediate Similarity	NPC472281
0.8415	Intermediate Similarity	NPC133065
0.8415	Intermediate Similarity	NPC18100
0.8415	Intermediate Similarity	NPC475985
0.8415	Intermediate Similarity	NPC473313
0.8415	Intermediate Similarity	NPC306321
0.8415	Intermediate Similarity	NPC207690
0.8415	Intermediate Similarity	NPC23298
0.8415	Intermediate Similarity	NPC205265
0.8415	Intermediate Similarity	NPC303460
0.8415	Intermediate Similarity	NPC146134
0.8415	Intermediate Similarity	NPC101769
0.8415	Intermediate Similarity	NPC189473
0.8415	Intermediate Similarity	NPC329669
0.8415	Intermediate Similarity	NPC472278
0.8412	Intermediate Similarity	NPC120102
0.8408	Intermediate Similarity	NPC287395
0.8408	Intermediate Similarity	NPC183655
0.8408	Intermediate Similarity	NPC476058
0.8405	Intermediate Similarity	NPC475883
0.8405	Intermediate Similarity	NPC278427
0.8405	Intermediate Similarity	NPC266314
0.8405	Intermediate Similarity	NPC474187
0.8405	Intermediate Similarity	NPC474351
0.8405	Intermediate Similarity	NPC474186
0.8395	Intermediate Similarity	NPC95936
0.8395	Intermediate Similarity	NPC85121
0.8395	Intermediate Similarity	NPC315157
0.8395	Intermediate Similarity	NPC185258
0.8395	Intermediate Similarity	NPC172770
0.8395	Intermediate Similarity	NPC250214
0.8385	Intermediate Similarity	NPC68093
0.8385	Intermediate Similarity	NPC138243
0.8385	Intermediate Similarity	NPC191146
0.8385	Intermediate Similarity	NPC115853
0.8383	Intermediate Similarity	NPC101107
0.8383	Intermediate Similarity	NPC472276
0.8383	Intermediate Similarity	NPC124470
0.8383	Intermediate Similarity	NPC109827
0.8382	Intermediate Similarity	NPC240808
0.8377	Intermediate Similarity	NPC11314
0.8375	Intermediate Similarity	NPC250557
0.8375	Intermediate Similarity	NPC89474
0.8375	Intermediate Similarity	NPC127172
0.8375	Intermediate Similarity	NPC124714
0.8373	Intermediate Similarity	NPC6588
0.8373	Intermediate Similarity	NPC117854
0.8373	Intermediate Similarity	NPC477154
0.8365	Intermediate Similarity	NPC45291
0.8365	Intermediate Similarity	NPC75377
0.8365	Intermediate Similarity	NPC19980
0.8365	Intermediate Similarity	NPC272566
0.8364	Intermediate Similarity	NPC472277
0.8364	Intermediate Similarity	NPC39306
0.8354	Intermediate Similarity	NPC134293
0.8354	Intermediate Similarity	NPC52204
0.8354	Intermediate Similarity	NPC144843
0.8354	Intermediate Similarity	NPC81679
0.8354	Intermediate Similarity	NPC229632
0.8353	Intermediate Similarity	NPC221820
0.8344	Intermediate Similarity	NPC119660
0.8344	Intermediate Similarity	NPC246478
0.8344	Intermediate Similarity	NPC36217
0.8344	Intermediate Similarity	NPC471690
0.8344	Intermediate Similarity	NPC297212
0.8344	Intermediate Similarity	NPC200746
0.8344	Intermediate Similarity	NPC476980
0.8344	Intermediate Similarity	NPC93034
0.8343	Intermediate Similarity	NPC139350
0.8343	Intermediate Similarity	NPC227906
0.8333	Intermediate Similarity	NPC161960
0.8333	Intermediate Similarity	NPC136674
0.8333	Intermediate Similarity	NPC96167
0.8333	Intermediate Similarity	NPC225351
0.8333	Intermediate Similarity	NPC304008
0.8333	Intermediate Similarity	NPC472910
0.8333	Intermediate Similarity	NPC223787
0.8333	Intermediate Similarity	NPC472911

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 NPC276815 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	1130
0.2-0.3	2198
0.3-0.4	2721
0.4-0.5	1664
0.5-0.6	718
0.6-0.7	272
0.7-0.8	71
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8313	Intermediate Similarity	NPD7473	Discontinued
0.8261	Intermediate Similarity	NPD2801	Approved
0.8242	Intermediate Similarity	NPD6232	Discontinued
0.8217	Intermediate Similarity	NPD2533	Approved
0.8217	Intermediate Similarity	NPD2534	Approved
0.8217	Intermediate Similarity	NPD2532	Approved
0.8092	Intermediate Similarity	NPD6651	Approved
0.8037	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2800	Approved
0.7975	Intermediate Similarity	NPD1934	Approved
0.7939	Intermediate Similarity	NPD3882	Suspended
0.7904	Intermediate Similarity	NPD5494	Approved
0.7702	Intermediate Similarity	NPD1511	Approved
0.7688	Intermediate Similarity	NPD5844	Phase 1
0.7647	Intermediate Similarity	NPD6959	Discontinued
0.763	Intermediate Similarity	NPD3818	Discontinued
0.7616	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6166	Phase 2
0.7616	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD1512	Approved
0.7602	Intermediate Similarity	NPD5710	Approved
0.7602	Intermediate Similarity	NPD5711	Approved
0.7546	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD4380	Phase 2
0.7516	Intermediate Similarity	NPD1607	Approved
0.75	Intermediate Similarity	NPD1465	Phase 2
0.7459	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3817	Phase 2
0.7443	Intermediate Similarity	NPD7074	Phase 3
0.7427	Intermediate Similarity	NPD6234	Discontinued
0.7425	Intermediate Similarity	NPD6599	Discontinued
0.7421	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7819	Suspended
0.7389	Intermediate Similarity	NPD1240	Approved
0.7389	Intermediate Similarity	NPD943	Approved
0.7386	Intermediate Similarity	NPD7054	Approved
0.7375	Intermediate Similarity	NPD2935	Discontinued
0.7345	Intermediate Similarity	NPD7472	Approved
0.7341	Intermediate Similarity	NPD1247	Approved
0.7337	Intermediate Similarity	NPD37	Approved
0.7333	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1510	Phase 2
0.7273	Intermediate Similarity	NPD7390	Discontinued
0.7267	Intermediate Similarity	NPD7075	Discontinued
0.7267	Intermediate Similarity	NPD6099	Approved
0.7267	Intermediate Similarity	NPD6100	Approved
0.7251	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7199	Phase 2
0.7229	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4967	Phase 2
0.7209	Intermediate Similarity	NPD4965	Approved
0.7209	Intermediate Similarity	NPD4966	Approved
0.7207	Intermediate Similarity	NPD6797	Phase 2
0.7198	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7251	Discontinued
0.7167	Intermediate Similarity	NPD6559	Discontinued
0.7159	Intermediate Similarity	NPD3926	Phase 2
0.7159	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD6801	Discontinued
0.7127	Intermediate Similarity	NPD7808	Phase 3
0.7125	Intermediate Similarity	NPD230	Phase 1
0.7117	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1549	Phase 2
0.7069	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6799	Approved
0.7059	Intermediate Similarity	NPD3226	Approved
0.7041	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD919	Approved
0.7017	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2346	Discontinued
0.7	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4628	Phase 3
0.6988	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3027	Phase 3
0.6977	Remote Similarity	NPD7411	Suspended
0.6971	Remote Similarity	NPD3749	Approved
0.6957	Remote Similarity	NPD3620	Phase 2
0.6957	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5402	Approved
0.6951	Remote Similarity	NPD2796	Approved
0.6927	Remote Similarity	NPD6778	Approved
0.6927	Remote Similarity	NPD6779	Approved
0.6927	Remote Similarity	NPD6777	Approved
0.6927	Remote Similarity	NPD6776	Approved
0.6927	Remote Similarity	NPD6781	Approved
0.6927	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6782	Approved
0.6927	Remote Similarity	NPD6780	Approved
0.6919	Remote Similarity	NPD7028	Phase 2
0.6886	Remote Similarity	NPD3750	Approved
0.6885	Remote Similarity	NPD7685	Pre-registration
0.6882	Remote Similarity	NPD8150	Discontinued
0.6882	Remote Similarity	NPD8434	Phase 2
0.686	Remote Similarity	NPD7458	Discontinued
0.6855	Remote Similarity	NPD9494	Approved
0.6854	Remote Similarity	NPD8127	Discontinued
0.6842	Remote Similarity	NPD920	Approved
0.6836	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7435	Discontinued
0.6818	Remote Similarity	NPD7768	Phase 2
0.6818	Remote Similarity	NPD8151	Discontinued
0.6811	Remote Similarity	NPD8312	Approved
0.6811	Remote Similarity	NPD8313	Approved
0.681	Remote Similarity	NPD447	Suspended
0.68	Remote Similarity	NPD5761	Phase 2
0.68	Remote Similarity	NPD5760	Phase 2
0.6788	Remote Similarity	NPD2799	Discontinued
0.6786	Remote Similarity	NPD7003	Approved
0.6786	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6535	Approved
0.6754	Remote Similarity	NPD6534	Approved
0.675	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5408	Approved
0.6747	Remote Similarity	NPD5405	Approved
0.6747	Remote Similarity	NPD5406	Approved
0.6747	Remote Similarity	NPD5404	Approved
0.6747	Remote Similarity	NPD1551	Phase 2
0.674	Remote Similarity	NPD2403	Approved
0.6735	Remote Similarity	NPD7698	Approved
0.6735	Remote Similarity	NPD7696	Phase 3
0.6735	Remote Similarity	NPD7697	Approved
0.6728	Remote Similarity	NPD7985	Registered
0.6726	Remote Similarity	NPD6674	Discontinued
0.6726	Remote Similarity	NPD1243	Approved
0.6725	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7286	Phase 2
0.6709	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2344	Approved
0.6703	Remote Similarity	NPD7240	Approved
0.6701	Remote Similarity	NPD7870	Phase 2
0.6701	Remote Similarity	NPD7871	Phase 2
0.6687	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6823	Phase 2
0.6683	Remote Similarity	NPD7701	Phase 2
0.6667	Remote Similarity	NPD7801	Approved
0.6667	Remote Similarity	NPD1876	Approved
0.6667	Remote Similarity	NPD6696	Suspended
0.6667	Remote Similarity	NPD5978	Approved
0.6667	Remote Similarity	NPD3751	Discontinued
0.6667	Remote Similarity	NPD5977	Approved
0.6649	Remote Similarity	NPD5953	Discontinued
0.6649	Remote Similarity	NPD7699	Phase 2
0.6649	Remote Similarity	NPD7700	Phase 2
0.6646	Remote Similarity	NPD9269	Phase 2
0.6646	Remote Similarity	NPD1613	Approved
0.6646	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3972	Approved
0.6631	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7229	Phase 3
0.663	Remote Similarity	NPD3787	Discontinued
0.6628	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD2654	Approved
0.6627	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD1470	Approved
0.6623	Remote Similarity	NPD7340	Approved
0.6617	Remote Similarity	NPD7874	Approved
0.6617	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD3300	Phase 2
0.6602	Remote Similarity	NPD4111	Phase 1
0.6602	Remote Similarity	NPD4665	Approved
0.6593	Remote Similarity	NPD5242	Approved
0.659	Remote Similarity	NPD6273	Approved
0.6588	Remote Similarity	NPD8166	Discontinued
0.6588	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4110	Phase 3
0.6587	Remote Similarity	NPD3748	Approved
0.6584	Remote Similarity	NPD7783	Phase 2
0.6584	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD1201	Approved
0.6573	Remote Similarity	NPD5353	Approved
0.6564	Remote Similarity	NPD4625	Phase 3
0.6562	Remote Similarity	NPD1283	Approved
0.6561	Remote Similarity	NPD3019	Approved
0.6561	Remote Similarity	NPD2932	Approved
0.6552	Remote Similarity	NPD5403	Approved
0.655	Remote Similarity	NPD2309	Approved
0.655	Remote Similarity	NPD6190	Approved
0.6548	Remote Similarity	NPD2493	Approved
0.6548	Remote Similarity	NPD2494	Approved
0.6538	Remote Similarity	NPD7907	Approved
0.6536	Remote Similarity	NPD1398	Phase 1
0.6533	Remote Similarity	NPD4582	Approved
0.6533	Remote Similarity	NPD4583	Approved
0.6528	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6212	Phase 3
0.6528	Remote Similarity	NPD6213	Phase 3

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