NPASS Compound

Structure

CID283301 OpenBabel06191716092D 25 27 0 0 1 0 0 0 0 0999 V2000 -4.2686 2.4023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9469 0.8795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8345 2.4539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7090 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 -1.0098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5602 -1.3595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6675 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8339 -0.4814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1682 1.4451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6677 0.9627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3347 0.9637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6673 0.9634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6675 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5012 1.4448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8337 1.4445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5015 -0.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3349 0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 0.9631 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8343 1.4442 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 2.5364 1.4640 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5011 2.4478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8336 2.4475 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5016 -1.4838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1686 -0.4804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 9 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 25 1 0 0 0 0 7 8 1 0 0 0 0 7 10 1 0 0 0 0 8 20 1 0 0 0 0 9 11 1 0 0 0 0 10 19 1 0 0 0 0 10 21 2 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 22 1 0 0 0 0 15 18 1 0 0 0 0 15 23 2 0 0 0 0 16 17 2 0 0 0 0 16 24 1 0 0 0 0 17 25 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:	346.18
Volume:	359.576
LogP:	3.583
LogD:	2.547
LogS:	-4.367
# Rotatable Bonds:	2
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.798
Synthetic Accessibility Score:	4.1
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.831
MDCK Permeability:	1.748245267663151e-05
Pgp-inhibitor:	0.303
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.725
30% Bioavailability (F30%):	0.312

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.25
Plasma Protein Binding (PPB):	96.32611083984375%
Volume Distribution (VD):	1.426
Pgp-substrate:	3.2831332683563232%

ADMET: Metabolism

CYP1A2-inhibitor:	0.589
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.271
CYP2C19-substrate:	0.854
CYP2C9-inhibitor:	0.669
CYP2C9-substrate:	0.89
CYP2D6-inhibitor:	0.285
CYP2D6-substrate:	0.257
CYP3A4-inhibitor:	0.424
CYP3A4-substrate:	0.58

ADMET: Excretion

Clearance (CL):	3.976
Half-life (T1/2):	0.211

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.192
Drug-inuced Liver Injury (DILI):	0.462
AMES Toxicity:	0.07
Rat Oral Acute Toxicity:	0.214
Maximum Recommended Daily Dose:	0.178
Skin Sensitization:	0.416
Carcinogencity:	0.14
Eye Corrosion:	0.003
Eye Irritation:	0.672
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC283301

Natural Product ID:	NPC283301
*Common Name:**	Taiwaniaquinol F
IUPAC Name:	(4aS,9aS)-5,8-dihydroxy-6-methoxy-1,1,4a-trimethyl-7-propan-2-yl-4,9a-dihydro-3H-fluorene-2,9-dione
Synonyms:	Taiwaniaquinol F
Standard InCHIKey:	VIRHHCMHBQFERA-UYAOXDASSA-N
Standard InCHI:	InChI=1S/C20H26O5/c1-9(2)11-14(22)12-13(16(24)17(11)25-6)20(5)8-7-10(21)19(3,4)18(20)15(12)23/h9,18,22,24H,7-8H2,1-6H3/t18-,20-/m1/s1
SMILES:	COc1c(C(C)C)c(O)c2c(c1O)[C@@]1(C)CCC(=O)C([C@H]1C2=O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087414
PubChem CID:	46880979
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[558160]

☑ 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 NPC283301 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	430
0.1-0.2	1918
0.2-0.3	3865
0.3-0.4	9685
0.4-0.5	9407
0.5-0.6	4570
0.6-0.7	6574
0.7-0.8	5598
0.8-0.85	576
0.85-0.9	53
0.9-0.95	16
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC276815
0.9933	High Similarity	NPC25850
0.9536	High Similarity	NPC273248
0.947	High Similarity	NPC161778
0.9216	High Similarity	NPC218628
0.9211	High Similarity	NPC50269
0.9119	High Similarity	NPC102372
0.9057	High Similarity	NPC173587
0.9057	High Similarity	NPC208120
0.9006	High Similarity	NPC232936
0.9	High Similarity	NPC146584
0.9	High Similarity	NPC21016
0.8974	High Similarity	NPC472048
0.8951	High Similarity	NPC213416
0.8938	High Similarity	NPC475055
0.8938	High Similarity	NPC29055
0.8868	High Similarity	NPC84571
0.8812	High Similarity	NPC311740
0.875	High Similarity	NPC155302
0.875	High Similarity	NPC161947
0.8742	High Similarity	NPC37543
0.8742	High Similarity	NPC92079
0.8742	High Similarity	NPC179732
0.8742	High Similarity	NPC199463
0.8704	High Similarity	NPC270837
0.8704	High Similarity	NPC220313
0.8704	High Similarity	NPC236132
0.8696	High Similarity	NPC87431
0.8696	High Similarity	NPC65746
0.8688	High Similarity	NPC45846
0.8679	High Similarity	NPC470762
0.8679	High Similarity	NPC14561
0.8679	High Similarity	NPC5379
0.8679	High Similarity	NPC48105
0.8679	High Similarity	NPC474167
0.8679	High Similarity	NPC77807
0.8642	High Similarity	NPC294965
0.8642	High Similarity	NPC470694
0.8634	High Similarity	NPC14353
0.8634	High Similarity	NPC56085
0.8634	High Similarity	NPC228785
0.8625	High Similarity	NPC178976
0.8589	High Similarity	NPC187491
0.8589	High Similarity	NPC319200
0.8589	High Similarity	NPC476822
0.858	High Similarity	NPC40491
0.858	High Similarity	NPC32694
0.858	High Similarity	NPC66288
0.858	High Similarity	NPC61010
0.858	High Similarity	NPC278052
0.8571	High Similarity	NPC100123
0.8553	High Similarity	NPC107109
0.8553	High Similarity	NPC477048
0.8553	High Similarity	NPC477047
0.8537	High Similarity	NPC473286
0.8537	High Similarity	NPC25361
0.8537	High Similarity	NPC26386
0.8537	High Similarity	NPC326520
0.8528	High Similarity	NPC215612
0.8526	High Similarity	NPC251188
0.8519	High Similarity	NPC119224
0.8519	High Similarity	NPC235018
0.8519	High Similarity	NPC80375
0.8519	High Similarity	NPC45146
0.8519	High Similarity	NPC320359
0.8509	High Similarity	NPC241904
0.8509	High Similarity	NPC217677
0.8509	High Similarity	NPC300727
0.8509	High Similarity	NPC165977
0.8503	High Similarity	NPC158226
0.85	High Similarity	NPC130589
0.85	High Similarity	NPC134287
0.85	High Similarity	NPC234485
0.8494	Intermediate Similarity	NPC165979
0.8494	Intermediate Similarity	NPC163130
0.8485	Intermediate Similarity	NPC37870
0.8485	Intermediate Similarity	NPC170245
0.8481	Intermediate Similarity	NPC472279
0.8481	Intermediate Similarity	NPC103509
0.8476	Intermediate Similarity	NPC197168
0.8476	Intermediate Similarity	NPC101769
0.8476	Intermediate Similarity	NPC7483
0.8476	Intermediate Similarity	NPC152659
0.8476	Intermediate Similarity	NPC248638
0.8476	Intermediate Similarity	NPC236521
0.8471	Intermediate Similarity	NPC15329
0.8471	Intermediate Similarity	NPC131451
0.8466	Intermediate Similarity	NPC472275
0.8457	Intermediate Similarity	NPC476242
0.8457	Intermediate Similarity	NPC235448
0.8447	Intermediate Similarity	NPC274730
0.8447	Intermediate Similarity	NPC142339
0.8438	Intermediate Similarity	NPC93552
0.8438	Intermediate Similarity	NPC127172
0.8434	Intermediate Similarity	NPC126204
0.8424	Intermediate Similarity	NPC239752
0.8424	Intermediate Similarity	NPC275780
0.8424	Intermediate Similarity	NPC472450
0.8418	Intermediate Similarity	NPC303989
0.8418	Intermediate Similarity	NPC102003
0.8418	Intermediate Similarity	NPC92722
0.8418	Intermediate Similarity	NPC134293
0.8415	Intermediate Similarity	NPC25152
0.8412	Intermediate Similarity	NPC77179
0.8412	Intermediate Similarity	NPC23553
0.8405	Intermediate Similarity	NPC475886
0.8405	Intermediate Similarity	NPC474287
0.8395	Intermediate Similarity	NPC236796
0.8395	Intermediate Similarity	NPC36852
0.8395	Intermediate Similarity	NPC302258
0.8395	Intermediate Similarity	NPC469584
0.8395	Intermediate Similarity	NPC262286
0.8395	Intermediate Similarity	NPC180011
0.8395	Intermediate Similarity	NPC219867
0.8395	Intermediate Similarity	NPC79053
0.8395	Intermediate Similarity	NPC78225
0.8395	Intermediate Similarity	NPC78103
0.8385	Intermediate Similarity	NPC39184
0.8383	Intermediate Similarity	NPC475805
0.8383	Intermediate Similarity	NPC476637
0.8383	Intermediate Similarity	NPC99613
0.8383	Intermediate Similarity	NPC49487
0.8375	Intermediate Similarity	NPC312338
0.8375	Intermediate Similarity	NPC149889
0.8375	Intermediate Similarity	NPC20337
0.8373	Intermediate Similarity	NPC29160
0.8373	Intermediate Similarity	NPC472452
0.8373	Intermediate Similarity	NPC39091
0.8372	Intermediate Similarity	NPC246153
0.8372	Intermediate Similarity	NPC182693
0.8372	Intermediate Similarity	NPC228209
0.8372	Intermediate Similarity	NPC240508
0.8365	Intermediate Similarity	NPC294646
0.8364	Intermediate Similarity	NPC303460
0.8364	Intermediate Similarity	NPC473313
0.8364	Intermediate Similarity	NPC23298
0.8364	Intermediate Similarity	NPC207690
0.8364	Intermediate Similarity	NPC475985
0.8364	Intermediate Similarity	NPC472278
0.8364	Intermediate Similarity	NPC146134
0.8364	Intermediate Similarity	NPC306321
0.8364	Intermediate Similarity	NPC18100
0.8364	Intermediate Similarity	NPC472281
0.8364	Intermediate Similarity	NPC329669
0.8364	Intermediate Similarity	NPC133065
0.8364	Intermediate Similarity	NPC205265
0.8364	Intermediate Similarity	NPC189473
0.8363	Intermediate Similarity	NPC120102
0.8354	Intermediate Similarity	NPC474187
0.8354	Intermediate Similarity	NPC474186
0.8354	Intermediate Similarity	NPC474351
0.8354	Intermediate Similarity	NPC476058
0.8354	Intermediate Similarity	NPC475883
0.8354	Intermediate Similarity	NPC287395
0.8354	Intermediate Similarity	NPC183655
0.8354	Intermediate Similarity	NPC266314
0.8354	Intermediate Similarity	NPC278427
0.8344	Intermediate Similarity	NPC477410
0.8344	Intermediate Similarity	NPC185258
0.8344	Intermediate Similarity	NPC250214
0.8344	Intermediate Similarity	NPC95936
0.8344	Intermediate Similarity	NPC172770
0.8344	Intermediate Similarity	NPC315157
0.8344	Intermediate Similarity	NPC85121
0.8333	Intermediate Similarity	NPC68093
0.8333	Intermediate Similarity	NPC109827
0.8333	Intermediate Similarity	NPC115853
0.8333	Intermediate Similarity	NPC101107
0.8333	Intermediate Similarity	NPC191146
0.8333	Intermediate Similarity	NPC472276
0.8333	Intermediate Similarity	NPC240808
0.8333	Intermediate Similarity	NPC124470
0.8333	Intermediate Similarity	NPC138243
0.8323	Intermediate Similarity	NPC6588
0.8323	Intermediate Similarity	NPC250557
0.8323	Intermediate Similarity	NPC477154
0.8323	Intermediate Similarity	NPC11314
0.8323	Intermediate Similarity	NPC89474
0.8323	Intermediate Similarity	NPC124714
0.8323	Intermediate Similarity	NPC117854
0.8323	Intermediate Similarity	NPC234331
0.8313	Intermediate Similarity	NPC19980
0.8313	Intermediate Similarity	NPC272566
0.8313	Intermediate Similarity	NPC472277
0.8313	Intermediate Similarity	NPC302783
0.8313	Intermediate Similarity	NPC39306
0.8313	Intermediate Similarity	NPC75377
0.8313	Intermediate Similarity	NPC473201
0.8313	Intermediate Similarity	NPC45291
0.8304	Intermediate Similarity	NPC221820
0.8303	Intermediate Similarity	NPC81679
0.8303	Intermediate Similarity	NPC52204
0.8303	Intermediate Similarity	NPC144843
0.8303	Intermediate Similarity	NPC229632
0.8294	Intermediate Similarity	NPC139350
0.8294	Intermediate Similarity	NPC245975
0.8294	Intermediate Similarity	NPC227906
0.8293	Intermediate Similarity	NPC185617
0.8293	Intermediate Similarity	NPC200746
0.8293	Intermediate Similarity	NPC246478

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 NPC283301 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	1144
0.2-0.3	2222
0.3-0.4	2730
0.4-0.5	1641
0.5-0.6	708
0.6-0.7	260
0.7-0.8	66
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
0.8373	Intermediate Similarity	NPD7473	Discontinued
0.8303	Intermediate Similarity	NPD6232	Discontinued
0.821	Intermediate Similarity	NPD2801	Approved
0.8165	Intermediate Similarity	NPD2533	Approved
0.8165	Intermediate Similarity	NPD2532	Approved
0.8165	Intermediate Similarity	NPD2534	Approved
0.8039	Intermediate Similarity	NPD6651	Approved
0.7988	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD2800	Approved
0.7927	Intermediate Similarity	NPD1934	Approved
0.7892	Intermediate Similarity	NPD3882	Suspended
0.7857	Intermediate Similarity	NPD5494	Approved
0.7654	Intermediate Similarity	NPD1511	Approved
0.7644	Intermediate Similarity	NPD5844	Phase 1
0.7602	Intermediate Similarity	NPD6959	Discontinued
0.7586	Intermediate Similarity	NPD3818	Discontinued
0.7572	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD6166	Phase 2
0.7572	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1512	Approved
0.7558	Intermediate Similarity	NPD5711	Approved
0.7558	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4380	Phase 2
0.7484	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1607	Approved
0.7456	Intermediate Similarity	NPD1465	Phase 2
0.7418	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD3817	Phase 2
0.7401	Intermediate Similarity	NPD7074	Phase 3
0.7384	Intermediate Similarity	NPD6234	Discontinued
0.7381	Intermediate Similarity	NPD6599	Discontinued
0.7374	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7819	Suspended
0.7345	Intermediate Similarity	NPD7054	Approved
0.7342	Intermediate Similarity	NPD1240	Approved
0.7342	Intermediate Similarity	NPD943	Approved
0.7329	Intermediate Similarity	NPD2935	Discontinued
0.7303	Intermediate Similarity	NPD7472	Approved
0.7299	Intermediate Similarity	NPD1247	Approved
0.7294	Intermediate Similarity	NPD37	Approved
0.7289	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1510	Phase 2
0.7267	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7390	Discontinued
0.7225	Intermediate Similarity	NPD7075	Discontinued
0.7222	Intermediate Similarity	NPD6099	Approved
0.7222	Intermediate Similarity	NPD6100	Approved
0.7216	Intermediate Similarity	NPD3926	Phase 2
0.7209	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7199	Phase 2
0.7186	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4967	Phase 2
0.7168	Intermediate Similarity	NPD4965	Approved
0.7168	Intermediate Similarity	NPD4966	Approved
0.7167	Intermediate Similarity	NPD6797	Phase 2
0.7158	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7251	Discontinued
0.7127	Intermediate Similarity	NPD6559	Discontinued
0.7119	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3226	Approved
0.7107	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7228	Approved
0.7093	Intermediate Similarity	NPD6801	Discontinued
0.7088	Intermediate Similarity	NPD7808	Phase 3
0.7081	Intermediate Similarity	NPD230	Phase 1
0.7073	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1549	Phase 2
0.7029	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6799	Approved
0.7	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD919	Approved
0.6979	Remote Similarity	NPD6779	Approved
0.6979	Remote Similarity	NPD6778	Approved
0.6979	Remote Similarity	NPD6776	Approved
0.6979	Remote Similarity	NPD6780	Approved
0.6979	Remote Similarity	NPD6782	Approved
0.6979	Remote Similarity	NPD6777	Approved
0.6979	Remote Similarity	NPD6781	Approved
0.6978	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2346	Discontinued
0.6961	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4628	Phase 3
0.6946	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3027	Phase 3
0.6936	Remote Similarity	NPD7411	Suspended
0.6935	Remote Similarity	NPD8434	Phase 2
0.6932	Remote Similarity	NPD3749	Approved
0.6914	Remote Similarity	NPD5402	Approved
0.6914	Remote Similarity	NPD3620	Phase 2
0.6914	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD2796	Approved
0.6893	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7028	Phase 2
0.6872	Remote Similarity	NPD7435	Discontinued
0.6869	Remote Similarity	NPD8151	Discontinued
0.6848	Remote Similarity	NPD7685	Pre-registration
0.6845	Remote Similarity	NPD3750	Approved
0.6845	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD8150	Discontinued
0.6821	Remote Similarity	NPD7458	Discontinued
0.6816	Remote Similarity	NPD8127	Discontinued
0.6813	Remote Similarity	NPD9494	Approved
0.6806	Remote Similarity	NPD6535	Approved
0.6806	Remote Similarity	NPD6534	Approved
0.6802	Remote Similarity	NPD920	Approved
0.6796	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7985	Registered
0.6786	Remote Similarity	NPD7696	Phase 3
0.6786	Remote Similarity	NPD7698	Approved
0.6786	Remote Similarity	NPD7697	Approved
0.678	Remote Similarity	NPD7768	Phase 2
0.6774	Remote Similarity	NPD8312	Approved
0.6774	Remote Similarity	NPD8313	Approved
0.6768	Remote Similarity	NPD447	Suspended
0.6766	Remote Similarity	NPD2344	Approved
0.6761	Remote Similarity	NPD5761	Phase 2
0.6761	Remote Similarity	NPD5760	Phase 2
0.6751	Remote Similarity	NPD7871	Phase 2
0.6751	Remote Similarity	NPD7870	Phase 2
0.6747	Remote Similarity	NPD2799	Discontinued
0.6746	Remote Similarity	NPD7003	Approved
0.6734	Remote Similarity	NPD7701	Phase 2
0.673	Remote Similarity	NPD1876	Approved
0.6725	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD3751	Discontinued
0.672	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7801	Approved
0.6708	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5406	Approved
0.6707	Remote Similarity	NPD5405	Approved
0.6707	Remote Similarity	NPD5408	Approved
0.6707	Remote Similarity	NPD5404	Approved
0.6707	Remote Similarity	NPD1551	Phase 2
0.6703	Remote Similarity	NPD2403	Approved
0.6703	Remote Similarity	NPD5953	Discontinued
0.6701	Remote Similarity	NPD7700	Phase 2
0.6701	Remote Similarity	NPD7699	Phase 2
0.6687	Remote Similarity	NPD1470	Approved
0.6686	Remote Similarity	NPD6674	Discontinued
0.6686	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1243	Approved
0.6685	Remote Similarity	NPD7286	Phase 2
0.6667	Remote Similarity	NPD7874	Approved
0.6667	Remote Similarity	NPD7240	Approved
0.6667	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6823	Phase 2
0.6649	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5978	Approved
0.6629	Remote Similarity	NPD5977	Approved
0.6625	Remote Similarity	NPD6696	Suspended
0.6608	Remote Similarity	NPD2309	Approved
0.6606	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1613	Approved
0.6604	Remote Similarity	NPD9269	Phase 2
0.6604	Remote Similarity	NPD3972	Approved
0.6596	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3787	Discontinued
0.6593	Remote Similarity	NPD7229	Phase 3
0.659	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD2654	Approved
0.6588	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7340	Approved
0.658	Remote Similarity	NPD6213	Phase 3
0.658	Remote Similarity	NPD6212	Phase 3
0.658	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.657	Remote Similarity	NPD3300	Phase 2
0.657	Remote Similarity	NPD4665	Approved
0.657	Remote Similarity	NPD4111	Phase 1
0.6557	Remote Similarity	NPD5242	Approved
0.6552	Remote Similarity	NPD7783	Phase 2
0.6552	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6273	Approved
0.655	Remote Similarity	NPD8166	Discontinued
0.655	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.655	Remote Similarity	NPD4110	Phase 3
0.6548	Remote Similarity	NPD3748	Approved
0.6541	Remote Similarity	NPD1201	Approved
0.6536	Remote Similarity	NPD5353	Approved
0.6524	Remote Similarity	NPD4625	Phase 3
0.6522	Remote Similarity	NPD1283	Approved
0.6519	Remote Similarity	NPD3019	Approved
0.6519	Remote Similarity	NPD2932	Approved
0.6515	Remote Similarity	NPD2494	Approved
0.6515	Remote Similarity	NPD2493	Approved
0.6514	Remote Similarity	NPD5403	Approved
0.6512	Remote Similarity	NPD6190	Approved
0.6507	Remote Similarity	NPD7907	Approved
0.65	Remote Similarity	NPD4583	Approved
0.65	Remote Similarity	NPD4582	Approved
0.6494	Remote Similarity	NPD1398	Phase 1

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