NPASS Compound

Structure

NPC474140 OpenBabel07101718242D 33 35 0 0 1 0 0 0 0 0999 V2000 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 0.3660 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 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 -1.5388 0.5000 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 3.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 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 5.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5180 5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1871 5.1132 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2601 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9000 3.9543 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5981 1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8270 6.8074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2308 4.6974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 2 0 0 0 0 2 20 1 0 0 0 0 6 29 1 0 0 0 0 8 13 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 24 1 0 0 0 0 10 27 2 0 0 0 0 11 14 1 0 0 0 0 11 25 1 0 0 0 0 12 15 1 0 0 0 0 12 26 1 0 0 0 0 13 28 1 0 0 0 0 14 30 1 0 0 0 0 15 29 1 0 0 0 0 16 31 1 0 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 18 23 1 0 0 0 0 19 21 1 0 0 0 0 19 32 1 0 0 0 0 20 24 1 0 0 0 0 21 3 1 1 0 0 0 22 4 1 6 0 0 0 22 25 1 0 0 0 0 23 33 1 1 0 0 0 24 28 1 6 0 0 0 25 29 1 6 0 0 0 26 27 1 0 0 0 0 26 28 1 1 0 0 0 27 30 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 6 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.39
Volume:	522.864
LogP:	6.019
LogD:	4.7
LogS:	-5.551
# Rotatable Bonds:	10
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.325
Synthetic Accessibility Score:	5.06
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.678
MDCK Permeability:	7.966683369886596e-06
Pgp-inhibitor:	0.819
Pgp-substrate:	0.157
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.84
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.199
Plasma Protein Binding (PPB):	94.89791107177734%
Volume Distribution (VD):	1.09
Pgp-substrate:	1.9237449169158936%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.243
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.893
CYP2C9-inhibitor:	0.256
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.147
CYP3A4-inhibitor:	0.904
CYP3A4-substrate:	0.47

ADMET: Excretion

Clearance (CL):	8.057
Half-life (T1/2):	0.123

ADMET: Toxicity

hERG Blockers:	0.146
Human Hepatotoxicity (H-HT):	0.264
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.703
Skin Sensitization:	0.906
Carcinogencity:	0.115
Eye Corrosion:	0.544
Eye Irritation:	0.189
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC474140

Natural Product ID:	NPC474140
*Common Name:**	(2R,4S,6R)-6-[(3R,3Ar,5As,6S,7S,9Br)-6-(3-Hydroxypropyl)-3A,6,9B-Trimethyl-7-Prop-1-En-2-Yl-1,2,3,4,5,5A,7,8-Octahydrocyclopenta[A]Naphthalen-3-Yl]-2-Methylheptane-1,4-Diol
IUPAC Name:	(2R,4S,6R)-6-[(3R,3aR,5aS,6S,7S,9bR)-6-(3-hydroxypropyl)-3a,6,9b-trimethyl-7-prop-1-en-2-yl-1,2,3,4,5,5a,7,8-octahydrocyclopenta[a]naphthalen-3-yl]-2-methylheptane-1,4-diol
Synonyms:
Standard InCHIKey:	JFEIXQKYVJTKKW-KYELGKBTSA-N
Standard InCHI:	InChI=1S/C30H52O3/c1-20(2)24-9-10-27-26(28(24,5)13-8-16-31)12-15-29(6)25(11-14-30(27,29)7)22(4)18-23(33)17-21(3)19-32/h10,21-26,31-33H,1,8-9,11-19H2,2-7H3/t21-,22-,23-,24+,25-,26-,28+,29-,30+/m1/s1
SMILES:	CC(CC(CC(C)C1CCC2(C1(CCC3C2=CCC(C3(C)CCCO)C(=C)C)C)C)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462848
PubChem CID:	10961552
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO23553	Abies sachalinensis	Species	Pinaceae	Eukaryota	Barks	n.a.	n.a.	PMID[12444693]
NPO23553	Abies sachalinensis	Species	Pinaceae	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
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1044	Individual Protein	DNA topoisomerase II alpha	Homo sapiens	IC50	=	50400.0	nM	PMID[489123]

☑ 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 NPC474140 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	135
0.1-0.2	1268
0.2-0.3	9086
0.3-0.4	14427
0.4-0.5	6671
0.5-0.6	6224
0.6-0.7	3661
0.7-0.8	1031
0.8-0.85	104
0.85-0.9	84
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9296	High Similarity	NPC107059
0.9296	High Similarity	NPC321016
0.9296	High Similarity	NPC321381
0.9167	High Similarity	NPC318495
0.9167	High Similarity	NPC155986
0.9167	High Similarity	NPC214570
0.9167	High Similarity	NPC198968
0.9155	High Similarity	NPC28657
0.9155	High Similarity	NPC162742
0.9155	High Similarity	NPC304309
0.9155	High Similarity	NPC22105
0.9155	High Similarity	NPC230301
0.9155	High Similarity	NPC136188
0.9155	High Similarity	NPC141071
0.9155	High Similarity	NPC285893
0.9155	High Similarity	NPC471723
0.9155	High Similarity	NPC257347
0.9155	High Similarity	NPC288035
0.9155	High Similarity	NPC134847
0.9118	High Similarity	NPC160209
0.9041	High Similarity	NPC474216
0.9041	High Similarity	NPC167037
0.9041	High Similarity	NPC244385
0.9041	High Similarity	NPC473943
0.9041	High Similarity	NPC477522
0.9041	High Similarity	NPC275910
0.9041	High Similarity	NPC477514
0.9041	High Similarity	NPC6978
0.9041	High Similarity	NPC138621
0.9041	High Similarity	NPC87604
0.9028	High Similarity	NPC113733
0.9028	High Similarity	NPC46160
0.9028	High Similarity	NPC240604
0.9028	High Similarity	NPC189883
0.9028	High Similarity	NPC73875
0.9028	High Similarity	NPC247325
0.9028	High Similarity	NPC244488
0.9028	High Similarity	NPC134330
0.9028	High Similarity	NPC470362
0.9028	High Similarity	NPC300324
0.9028	High Similarity	NPC202642
0.9028	High Similarity	NPC129165
0.8919	High Similarity	NPC328714
0.8919	High Similarity	NPC84694
0.8919	High Similarity	NPC30986
0.8919	High Similarity	NPC209430
0.8919	High Similarity	NPC1319
0.8919	High Similarity	NPC109546
0.8919	High Similarity	NPC273410
0.8919	High Similarity	NPC81306
0.8919	High Similarity	NPC143182
0.8919	High Similarity	NPC28862
0.8919	High Similarity	NPC47982
0.8919	High Similarity	NPC80530
0.8904	High Similarity	NPC34019
0.8889	High Similarity	NPC118508
0.8889	High Similarity	NPC121744
0.8889	High Similarity	NPC328104
0.8889	High Similarity	NPC319090
0.8889	High Similarity	NPC322353
0.8857	High Similarity	NPC34834
0.8841	High Similarity	NPC208999
0.8816	High Similarity	NPC1272
0.8816	High Similarity	NPC470614
0.88	High Similarity	NPC26117
0.88	High Similarity	NPC102253
0.88	High Similarity	NPC164840
0.88	High Similarity	NPC234193
0.88	High Similarity	NPC236237
0.88	High Similarity	NPC236112
0.88	High Similarity	NPC241290
0.88	High Similarity	NPC322313
0.88	High Similarity	NPC209944
0.8784	High Similarity	NPC76931
0.8784	High Similarity	NPC205455
0.8784	High Similarity	NPC186191
0.8784	High Similarity	NPC307965
0.8784	High Similarity	NPC285761
0.8784	High Similarity	NPC18603
0.8767	High Similarity	NPC237460
0.8767	High Similarity	NPC96319
0.875	High Similarity	NPC329090
0.875	High Similarity	NPC27395
0.8684	High Similarity	NPC82986
0.8684	High Similarity	NPC47761
0.8684	High Similarity	NPC470383
0.8684	High Similarity	NPC264245
0.8684	High Similarity	NPC474531
0.8684	High Similarity	NPC474731
0.8684	High Similarity	NPC23852
0.8684	High Similarity	NPC474683
0.8684	High Similarity	NPC474752
0.8684	High Similarity	NPC7505
0.8684	High Similarity	NPC209620
0.8684	High Similarity	NPC474759
0.863	High Similarity	NPC471468
0.8611	High Similarity	NPC201373
0.8611	High Similarity	NPC471799
0.8592	High Similarity	NPC475728
0.8592	High Similarity	NPC92801
0.859	High Similarity	NPC478102
0.859	High Similarity	NPC124172
0.8571	High Similarity	NPC50964
0.8571	High Similarity	NPC87489
0.8571	High Similarity	NPC202389
0.8571	High Similarity	NPC189972
0.8571	High Similarity	NPC30166
0.8571	High Similarity	NPC101462
0.8571	High Similarity	NPC201852
0.8571	High Similarity	NPC49964
0.8571	High Similarity	NPC5985
0.8571	High Similarity	NPC470049
0.8553	High Similarity	NPC13554
0.8533	High Similarity	NPC85346
0.8533	High Similarity	NPC318136
0.8533	High Similarity	NPC65897
0.8533	High Similarity	NPC302041
0.8514	High Similarity	NPC315261
0.8493	Intermediate Similarity	NPC469534
0.8493	Intermediate Similarity	NPC469593
0.8493	Intermediate Similarity	NPC471797
0.8493	Intermediate Similarity	NPC469533
0.8481	Intermediate Similarity	NPC474349
0.8481	Intermediate Similarity	NPC474189
0.8472	Intermediate Similarity	NPC242001
0.8472	Intermediate Similarity	NPC164022
0.8472	Intermediate Similarity	NPC167706
0.8462	Intermediate Similarity	NPC474634
0.8462	Intermediate Similarity	NPC475789
0.8462	Intermediate Similarity	NPC207013
0.8462	Intermediate Similarity	NPC470384
0.8462	Intermediate Similarity	NPC317458
0.8462	Intermediate Similarity	NPC110778
0.8462	Intermediate Similarity	NPC477818
0.8451	Intermediate Similarity	NPC167272
0.8451	Intermediate Similarity	NPC269877
0.8442	Intermediate Similarity	NPC6707
0.8429	Intermediate Similarity	NPC197805
0.8406	Intermediate Similarity	NPC238352
0.8406	Intermediate Similarity	NPC477009
0.84	Intermediate Similarity	NPC130136
0.8378	Intermediate Similarity	NPC291503
0.8378	Intermediate Similarity	NPC3403
0.8375	Intermediate Similarity	NPC24277
0.8356	Intermediate Similarity	NPC182717
0.8356	Intermediate Similarity	NPC68443
0.8354	Intermediate Similarity	NPC59453
0.8354	Intermediate Similarity	NPC33913
0.8354	Intermediate Similarity	NPC85774
0.8354	Intermediate Similarity	NPC473246
0.8354	Intermediate Similarity	NPC165064
0.8354	Intermediate Similarity	NPC474047
0.8354	Intermediate Similarity	NPC470077
0.8354	Intermediate Similarity	NPC185568
0.8354	Intermediate Similarity	NPC231310
0.8354	Intermediate Similarity	NPC214043
0.8354	Intermediate Similarity	NPC472265
0.8354	Intermediate Similarity	NPC205845
0.8354	Intermediate Similarity	NPC209802
0.8354	Intermediate Similarity	NPC82902
0.8354	Intermediate Similarity	NPC221758
0.8354	Intermediate Similarity	NPC238485
0.8333	Intermediate Similarity	NPC9161
0.8333	Intermediate Similarity	NPC49422
0.8333	Intermediate Similarity	NPC248886
0.8333	Intermediate Similarity	NPC20853
0.8333	Intermediate Similarity	NPC296701
0.8333	Intermediate Similarity	NPC145498
0.8333	Intermediate Similarity	NPC218616
0.831	Intermediate Similarity	NPC216460
0.8289	Intermediate Similarity	NPC300499
0.8289	Intermediate Similarity	NPC312328
0.8286	Intermediate Similarity	NPC286669
0.8286	Intermediate Similarity	NPC222366
0.8286	Intermediate Similarity	NPC476039
0.8272	Intermediate Similarity	NPC271967
0.8267	Intermediate Similarity	NPC274079
0.8267	Intermediate Similarity	NPC86305
0.8267	Intermediate Similarity	NPC477925
0.8267	Intermediate Similarity	NPC265588
0.8267	Intermediate Similarity	NPC14112
0.8267	Intermediate Similarity	NPC106432
0.8261	Intermediate Similarity	NPC309300
0.8261	Intermediate Similarity	NPC290367
0.8261	Intermediate Similarity	NPC225415
0.825	Intermediate Similarity	NPC274448
0.825	Intermediate Similarity	NPC266511
0.825	Intermediate Similarity	NPC157257
0.825	Intermediate Similarity	NPC474083
0.825	Intermediate Similarity	NPC471224
0.825	Intermediate Similarity	NPC318390
0.825	Intermediate Similarity	NPC474218
0.8243	Intermediate Similarity	NPC100334
0.8243	Intermediate Similarity	NPC477138
0.8243	Intermediate Similarity	NPC243342
0.8243	Intermediate Similarity	NPC91858
0.8235	Intermediate Similarity	NPC475251
0.8228	Intermediate Similarity	NPC193870
0.8228	Intermediate Similarity	NPC278648
0.8228	Intermediate Similarity	NPC476082

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 NPC474140 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	128
0.1-0.2	1702
0.2-0.3	4502
0.3-0.4	1989
0.4-0.5	416
0.5-0.6	164
0.6-0.7	173
0.7-0.8	56
0.8-0.85	15
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9155	High Similarity	NPD7339	Approved
0.9155	High Similarity	NPD6942	Approved
0.88	High Similarity	NPD7525	Registered
0.8767	High Similarity	NPD3701	Clinical (unspecified phase)
0.875	High Similarity	NPD6926	Approved
0.875	High Similarity	NPD6924	Approved
0.8514	High Similarity	NPD6933	Approved
0.8472	Intermediate Similarity	NPD4243	Approved
0.8451	Intermediate Similarity	NPD6922	Approved
0.8451	Intermediate Similarity	NPD6923	Approved
0.8354	Intermediate Similarity	NPD4786	Approved
0.8333	Intermediate Similarity	NPD7143	Approved
0.8333	Intermediate Similarity	NPD7144	Approved
0.8243	Intermediate Similarity	NPD4785	Approved
0.8243	Intermediate Similarity	NPD4784	Approved
0.8219	Intermediate Similarity	NPD7151	Approved
0.8219	Intermediate Similarity	NPD7152	Approved
0.8219	Intermediate Similarity	NPD7150	Approved
0.8182	Intermediate Similarity	NPD6929	Approved
0.8101	Intermediate Similarity	NPD3667	Approved
0.8077	Intermediate Similarity	NPD7509	Discontinued
0.8077	Intermediate Similarity	NPD6931	Approved
0.8077	Intermediate Similarity	NPD6930	Phase 2
0.7949	Intermediate Similarity	NPD7645	Phase 2
0.7922	Intermediate Similarity	NPD6932	Approved
0.7922	Intermediate Similarity	NPD5776	Phase 2
0.7922	Intermediate Similarity	NPD6925	Approved
0.7901	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD3133	Approved
0.7901	Intermediate Similarity	NPD3666	Approved
0.7901	Intermediate Similarity	NPD3665	Phase 1
0.7895	Intermediate Similarity	NPD5275	Approved
0.7895	Intermediate Similarity	NPD4190	Phase 3
0.7857	Intermediate Similarity	NPD5328	Approved
0.7848	Intermediate Similarity	NPD4748	Discontinued
0.7831	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7145	Approved
0.7778	Intermediate Similarity	NPD6695	Phase 3
0.7722	Intermediate Similarity	NPD4195	Approved
0.7722	Intermediate Similarity	NPD6683	Phase 2
0.7711	Intermediate Similarity	NPD5279	Phase 3
0.7711	Intermediate Similarity	NPD3618	Phase 1
0.7674	Intermediate Similarity	NPD6079	Approved
0.7625	Intermediate Similarity	NPD7514	Phase 3
0.7595	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6893	Approved
0.7586	Intermediate Similarity	NPD6399	Phase 3
0.7586	Intermediate Similarity	NPD4202	Approved
0.7531	Intermediate Similarity	NPD6902	Approved
0.7442	Intermediate Similarity	NPD4753	Phase 2
0.7439	Intermediate Similarity	NPD4223	Phase 3
0.7439	Intermediate Similarity	NPD4221	Approved
0.7436	Intermediate Similarity	NPD8264	Approved
0.7412	Intermediate Similarity	NPD7750	Discontinued
0.7412	Intermediate Similarity	NPD7524	Approved
0.7407	Intermediate Similarity	NPD7332	Phase 2
0.7381	Intermediate Similarity	NPD5329	Approved
0.7317	Intermediate Similarity	NPD6898	Phase 1
0.7262	Intermediate Similarity	NPD4197	Approved
0.7262	Intermediate Similarity	NPD3668	Phase 3
0.7253	Intermediate Similarity	NPD4755	Approved
0.7222	Intermediate Similarity	NPD368	Approved
0.7176	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5222	Approved
0.7143	Intermediate Similarity	NPD5221	Approved
0.7143	Intermediate Similarity	NPD4697	Phase 3
0.7143	Intermediate Similarity	NPD4788	Approved
0.7143	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5285	Approved
0.7097	Intermediate Similarity	NPD4700	Approved
0.7097	Intermediate Similarity	NPD4696	Approved
0.7097	Intermediate Similarity	NPD5286	Approved
0.7093	Intermediate Similarity	NPD4694	Approved
0.7093	Intermediate Similarity	NPD5280	Approved
0.7093	Intermediate Similarity	NPD6684	Approved
0.7093	Intermediate Similarity	NPD5205	Approved
0.7093	Intermediate Similarity	NPD4693	Phase 3
0.7093	Intermediate Similarity	NPD5330	Approved
0.7093	Intermediate Similarity	NPD6409	Approved
0.7093	Intermediate Similarity	NPD7521	Approved
0.7093	Intermediate Similarity	NPD7334	Approved
0.7093	Intermediate Similarity	NPD4690	Approved
0.7093	Intermediate Similarity	NPD5690	Phase 2
0.7093	Intermediate Similarity	NPD7146	Approved
0.7093	Intermediate Similarity	NPD4688	Approved
0.7093	Intermediate Similarity	NPD4689	Approved
0.7093	Intermediate Similarity	NPD4138	Approved
0.7079	Intermediate Similarity	NPD7087	Discontinued
0.7065	Intermediate Similarity	NPD6083	Phase 2
0.7065	Intermediate Similarity	NPD5173	Approved
0.7065	Intermediate Similarity	NPD6084	Phase 2
0.7045	Intermediate Similarity	NPD6051	Approved
0.7033	Intermediate Similarity	NPD4629	Approved
0.7033	Intermediate Similarity	NPD5210	Approved
0.7021	Intermediate Similarity	NPD5223	Approved
0.6951	Remote Similarity	NPD3617	Approved
0.6947	Remote Similarity	NPD5226	Approved
0.6947	Remote Similarity	NPD5225	Approved
0.6947	Remote Similarity	NPD4633	Approved
0.6947	Remote Similarity	NPD5211	Phase 2
0.6947	Remote Similarity	NPD5224	Approved
0.6932	Remote Similarity	NPD6672	Approved
0.6932	Remote Similarity	NPD4722	Approved
0.6932	Remote Similarity	NPD4723	Approved
0.6932	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6903	Approved
0.6932	Remote Similarity	NPD5737	Approved
0.6907	Remote Similarity	NPD7128	Approved
0.6907	Remote Similarity	NPD5739	Approved
0.6907	Remote Similarity	NPD6675	Approved
0.6907	Remote Similarity	NPD6402	Approved
0.6905	Remote Similarity	NPD4692	Approved
0.6905	Remote Similarity	NPD4139	Approved
0.6889	Remote Similarity	NPD7515	Phase 2
0.6889	Remote Similarity	NPD5281	Approved
0.6889	Remote Similarity	NPD5284	Approved
0.6875	Remote Similarity	NPD5174	Approved
0.6875	Remote Similarity	NPD4754	Approved
0.6875	Remote Similarity	NPD5175	Approved
0.6857	Remote Similarity	NPD342	Phase 1
0.6848	Remote Similarity	NPD5695	Phase 3
0.6809	Remote Similarity	NPD7638	Approved
0.6809	Remote Similarity	NPD5290	Discontinued
0.6804	Remote Similarity	NPD5141	Approved
0.6795	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7320	Approved
0.6768	Remote Similarity	NPD6881	Approved
0.6768	Remote Similarity	NPD6899	Approved
0.6747	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7639	Approved
0.6737	Remote Similarity	NPD7640	Approved
0.6735	Remote Similarity	NPD4767	Approved
0.6735	Remote Similarity	NPD4768	Approved
0.6711	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4787	Phase 1
0.6709	Remote Similarity	NPD4747	Approved
0.6705	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6098	Approved
0.6703	Remote Similarity	NPD7637	Suspended
0.6703	Remote Similarity	NPD8035	Phase 2
0.6703	Remote Similarity	NPD8034	Phase 2
0.67	Remote Similarity	NPD6373	Approved
0.67	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD5733	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6634	Remote Similarity	NPD6883	Approved
0.6634	Remote Similarity	NPD7102	Approved
0.6634	Remote Similarity	NPD7290	Approved
0.6632	Remote Similarity	NPD5696	Approved
0.6625	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4729	Approved
0.66	Remote Similarity	NPD6011	Approved
0.66	Remote Similarity	NPD4730	Approved
0.66	Remote Similarity	NPD5128	Approved
0.6593	Remote Similarity	NPD4096	Approved
0.6593	Remote Similarity	NPD7136	Phase 2
0.6588	Remote Similarity	NPD4695	Discontinued
0.6582	Remote Similarity	NPD4137	Phase 3
0.6569	Remote Similarity	NPD8130	Phase 1
0.6569	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6869	Approved
0.6569	Remote Similarity	NPD6617	Approved
0.6569	Remote Similarity	NPD6847	Approved
0.6569	Remote Similarity	NPD6649	Approved
0.6569	Remote Similarity	NPD6650	Approved
0.6559	Remote Similarity	NPD7748	Approved
0.6535	Remote Similarity	NPD6012	Approved
0.6535	Remote Similarity	NPD6014	Approved
0.6535	Remote Similarity	NPD6013	Approved
0.6526	Remote Similarity	NPD7902	Approved
0.6517	Remote Similarity	NPD4519	Discontinued
0.6517	Remote Similarity	NPD4623	Approved
0.6506	Remote Similarity	NPD1346	Approved
0.6505	Remote Similarity	NPD6882	Approved
0.6505	Remote Similarity	NPD8297	Approved
0.65	Remote Similarity	NPD4245	Approved
0.65	Remote Similarity	NPD4691	Approved
0.65	Remote Similarity	NPD4244	Approved
0.65	Remote Similarity	NPD4789	Approved
0.6484	Remote Similarity	NPD6904	Approved
0.6484	Remote Similarity	NPD6080	Approved
0.6484	Remote Similarity	NPD6673	Approved
0.6471	Remote Similarity	NPD5250	Approved
0.6471	Remote Similarity	NPD5248	Approved
0.6471	Remote Similarity	NPD5251	Approved
0.6471	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4634	Approved
0.6471	Remote Similarity	NPD5249	Phase 3
0.6471	Remote Similarity	NPD5169	Approved
0.6471	Remote Similarity	NPD5247	Approved
0.6471	Remote Similarity	NPD5135	Approved
0.6463	Remote Similarity	NPD4687	Approved
0.6463	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD6705	Phase 1
0.6452	Remote Similarity	NPD5133	Approved
0.6436	Remote Similarity	NPD5168	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