NPASS Compound

Structure

CID165064 OpenBabel06191715532D 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 1.0563 3.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4164 5.2327 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 -0.5909 3.0032 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 -0.9000 3.9543 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 4.0981 0.3660 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7473 4.4895 0.0000 C 0 0 0 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 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 -0.2308 4.6974 0.0000 C 0 0 2 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 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 -0.5398 5.6485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5981 -0.5000 0.0000 O 0 0 0 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 19 2 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 4 20 1 0 0 0 0 7 29 1 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 25 2 0 0 0 0 12 26 1 0 0 0 0 13 17 1 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 0 0 0 0 19 22 1 0 0 0 0 20 26 1 0 0 0 0 21 5 1 6 0 0 0 21 23 1 0 0 0 0 22 28 1 6 0 0 0 23 29 1 6 0 0 0 24 25 1 0 0 0 0 24 28 1 1 0 0 0 25 30 1 0 0 0 0 26 31 1 1 0 0 0 27 32 2 0 0 0 0 27 33 1 0 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	517.591
LogP:	6.442
LogD:	4.883
LogS:	-5.449
# Rotatable Bonds:	9
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.352
Synthetic Accessibility Score:	4.919
Fsp3:	0.767
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:	-5.136
MDCK Permeability:	9.164768016489688e-06
Pgp-inhibitor:	0.033
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.909
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.105
Plasma Protein Binding (PPB):	95.04717254638672%
Volume Distribution (VD):	0.665
Pgp-substrate:	4.839780330657959%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.368
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.88
CYP2C9-inhibitor:	0.149
CYP2C9-substrate:	0.883
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.697
CYP3A4-inhibitor:	0.228
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	3.353
Half-life (T1/2):	0.138

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.327
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.457
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.441
Carcinogencity:	0.242
Eye Corrosion:	0.542
Eye Irritation:	0.139
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC165064

Natural Product ID:	NPC165064
*Common Name:**	Seco-Coccinic Acid E
IUPAC Name:	3-[(3R,3aR,5aS,6S,7S,9bR)-3-[(2R,5R)-5-hydroxy-6-methylhept-6-en-2-yl]-3a,6,9b-trimethyl-7-prop-1-en-2-yl-1,2,3,4,5,5a,7,8-octahydrocyclopenta[a]naphthalen-6-yl]propanoic acid
Synonyms:	Seco-coccinic acid E
Standard InCHIKey:	ZMCRUDHUTIZNBA-XDZMNQSHSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-19(2)22-10-11-25-24(28(22,6)16-15-27(32)33)14-18-29(7)23(13-17-30(25,29)8)21(5)9-12-26(31)20(3)4/h11,21-24,26,31H,1,3,9-10,12-18H2,2,4-8H3,(H,32,33)/t21-,22+,23-,24-,26-,28+,29-,30+/m1/s1
SMILES:	C=C(C)[C@@H]1CC=C2[C@@H](CC[C@]3(C)[C@H](CC[C@@]23C)[C@H](C)CC[C@H](C(=C)C)O)[C@@]1(C)CCC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486082
PubChem CID:	24896697
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
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18027905]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18271558]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	roots	n.a.	n.a.	PMID[18491866]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590312]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24299567]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214125]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	Stems	n.a.	n.a.	PMID[27704807]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO912	Kadsura coccinea	Species	Schisandraceae	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
GI50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	42100.0	nM	PMID[575607]

☑ 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 NPC165064 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	136
0.1-0.2	942
0.2-0.3	4874
0.3-0.4	14754
0.4-0.5	7849
0.5-0.6	6133
0.6-0.7	5316
0.7-0.8	2270
0.8-0.85	322
0.85-0.9	90
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9268	High Similarity	NPC155011
0.9259	High Similarity	NPC476038
0.9259	High Similarity	NPC194937
0.9157	High Similarity	NPC474684
0.9157	High Similarity	NPC159046
0.9157	High Similarity	NPC233836
0.9157	High Similarity	NPC142361
0.9157	High Similarity	NPC187376
0.9146	High Similarity	NPC283733
0.9146	High Similarity	NPC471224
0.9146	High Similarity	NPC474083
0.9114	High Similarity	NPC477371
0.9059	High Similarity	NPC469400
0.9036	High Similarity	NPC55309
0.9036	High Similarity	NPC469994
0.9036	High Similarity	NPC28252
0.8966	High Similarity	NPC469406
0.8941	High Similarity	NPC102414
0.8941	High Similarity	NPC474704
0.8941	High Similarity	NPC84271
0.8941	High Similarity	NPC77168
0.8941	High Similarity	NPC155479
0.8941	High Similarity	NPC475921
0.8941	High Similarity	NPC214387
0.8929	High Similarity	NPC96496
0.8929	High Similarity	NPC167877
0.8929	High Similarity	NPC312215
0.8889	High Similarity	NPC477372
0.8889	High Similarity	NPC201912
0.8889	High Similarity	NPC147066
0.8889	High Similarity	NPC38350
0.8851	High Similarity	NPC243866
0.8837	High Similarity	NPC477149
0.8837	High Similarity	NPC477147
0.8824	High Similarity	NPC242864
0.8824	High Similarity	NPC294480
0.881	High Similarity	NPC212843
0.8795	High Similarity	NPC85774
0.8795	High Similarity	NPC221758
0.8795	High Similarity	NPC59453
0.8795	High Similarity	NPC82902
0.8795	High Similarity	NPC214043
0.8795	High Similarity	NPC473246
0.8795	High Similarity	NPC164577
0.878	High Similarity	NPC260956
0.878	High Similarity	NPC133391
0.8764	High Similarity	NPC472941
0.8764	High Similarity	NPC456
0.8764	High Similarity	NPC155676
0.875	High Similarity	NPC239098
0.875	High Similarity	NPC179028
0.8736	High Similarity	NPC189520
0.8736	High Similarity	NPC154101
0.8736	High Similarity	NPC45269
0.8721	High Similarity	NPC128496
0.8721	High Similarity	NPC54689
0.8721	High Similarity	NPC473999
0.8721	High Similarity	NPC310236
0.8721	High Similarity	NPC309603
0.8721	High Similarity	NPC2983
0.8706	High Similarity	NPC317590
0.8706	High Similarity	NPC136948
0.8706	High Similarity	NPC128644
0.869	High Similarity	NPC269638
0.869	High Similarity	NPC474218
0.8675	High Similarity	NPC69279
0.8675	High Similarity	NPC278648
0.8675	High Similarity	NPC310470
0.8675	High Similarity	NPC97913
0.8675	High Similarity	NPC215893
0.8675	High Similarity	NPC83569
0.8675	High Similarity	NPC477373
0.8675	High Similarity	NPC476082
0.8667	High Similarity	NPC107243
0.8667	High Similarity	NPC475894
0.8659	High Similarity	NPC473420
0.8652	High Similarity	NPC173875
0.8652	High Similarity	NPC318282
0.8652	High Similarity	NPC174948
0.8652	High Similarity	NPC469995
0.8652	High Similarity	NPC476174
0.8642	High Similarity	NPC158846
0.8636	High Similarity	NPC470376
0.8636	High Similarity	NPC470224
0.8636	High Similarity	NPC66429
0.8636	High Similarity	NPC470375
0.8636	High Similarity	NPC152897
0.8621	High Similarity	NPC471896
0.8621	High Similarity	NPC111585
0.8621	High Similarity	NPC48010
0.8621	High Similarity	NPC148414
0.8621	High Similarity	NPC69622
0.8621	High Similarity	NPC46281
0.8621	High Similarity	NPC175628
0.8605	High Similarity	NPC249889
0.8605	High Similarity	NPC183546
0.8605	High Similarity	NPC193843
0.8605	High Similarity	NPC247406
0.8605	High Similarity	NPC48866
0.8588	High Similarity	NPC474733
0.8588	High Similarity	NPC322159
0.8588	High Similarity	NPC475007
0.8588	High Similarity	NPC94755
0.8588	High Similarity	NPC474732
0.8588	High Similarity	NPC51014
0.8588	High Similarity	NPC31564
0.8588	High Similarity	NPC473226
0.8588	High Similarity	NPC145879
0.8588	High Similarity	NPC82979
0.8588	High Similarity	NPC474778
0.8588	High Similarity	NPC70661
0.8571	High Similarity	NPC48647
0.8571	High Similarity	NPC166745
0.8571	High Similarity	NPC235464
0.8571	High Similarity	NPC186810
0.8571	High Similarity	NPC472865
0.8571	High Similarity	NPC100391
0.8571	High Similarity	NPC197386
0.8571	High Similarity	NPC263974
0.8556	High Similarity	NPC328371
0.8554	High Similarity	NPC170985
0.8554	High Similarity	NPC151519
0.8554	High Similarity	NPC320514
0.8539	High Similarity	NPC7165
0.8523	High Similarity	NPC107690
0.8523	High Similarity	NPC86266
0.8523	High Similarity	NPC212301
0.8523	High Similarity	NPC110657
0.8523	High Similarity	NPC297265
0.8523	High Similarity	NPC475806
0.8523	High Similarity	NPC476187
0.8523	High Similarity	NPC473998
0.8523	High Similarity	NPC23434
0.8523	High Similarity	NPC26888
0.8519	High Similarity	NPC321514
0.8506	High Similarity	NPC472970
0.8506	High Similarity	NPC215029
0.8506	High Similarity	NPC474889
0.8506	High Similarity	NPC262858
0.8506	High Similarity	NPC472971
0.8506	High Similarity	NPC472240
0.8506	High Similarity	NPC474570
0.8506	High Similarity	NPC146554
0.8506	High Similarity	NPC476733
0.8506	High Similarity	NPC262043
0.8506	High Similarity	NPC281524
0.8488	Intermediate Similarity	NPC90652
0.8488	Intermediate Similarity	NPC475740
0.8488	Intermediate Similarity	NPC58063
0.8478	Intermediate Similarity	NPC218383
0.8478	Intermediate Similarity	NPC51370
0.8478	Intermediate Similarity	NPC287833
0.8478	Intermediate Similarity	NPC476274
0.8471	Intermediate Similarity	NPC52628
0.8471	Intermediate Similarity	NPC469948
0.8471	Intermediate Similarity	NPC202868
0.8471	Intermediate Similarity	NPC29447
0.8462	Intermediate Similarity	NPC57416
0.8462	Intermediate Similarity	NPC160817
0.8462	Intermediate Similarity	NPC320306
0.8452	Intermediate Similarity	NPC245866
0.8444	Intermediate Similarity	NPC45324
0.8444	Intermediate Similarity	NPC469599
0.8444	Intermediate Similarity	NPC162001
0.8444	Intermediate Similarity	NPC263347
0.8444	Intermediate Similarity	NPC222845
0.8434	Intermediate Similarity	NPC327002
0.8427	Intermediate Similarity	NPC69454
0.8427	Intermediate Similarity	NPC470254
0.8427	Intermediate Similarity	NPC477855
0.8427	Intermediate Similarity	NPC472930
0.8427	Intermediate Similarity	NPC170220
0.8427	Intermediate Similarity	NPC474736
0.8427	Intermediate Similarity	NPC141497
0.8427	Intermediate Similarity	NPC107674
0.8427	Intermediate Similarity	NPC472942
0.8427	Intermediate Similarity	NPC206810
0.8415	Intermediate Similarity	NPC196827
0.8415	Intermediate Similarity	NPC327674
0.8415	Intermediate Similarity	NPC274996
0.8409	Intermediate Similarity	NPC44240
0.8409	Intermediate Similarity	NPC123854
0.8409	Intermediate Similarity	NPC320026
0.8395	Intermediate Similarity	NPC74995
0.8391	Intermediate Similarity	NPC117122
0.8391	Intermediate Similarity	NPC16377
0.8391	Intermediate Similarity	NPC328313
0.8391	Intermediate Similarity	NPC470417
0.8391	Intermediate Similarity	NPC472870
0.8391	Intermediate Similarity	NPC471722
0.8387	Intermediate Similarity	NPC476240
0.8387	Intermediate Similarity	NPC476223
0.8387	Intermediate Similarity	NPC224720
0.8387	Intermediate Similarity	NPC472924
0.8375	Intermediate Similarity	NPC476795
0.8372	Intermediate Similarity	NPC472869
0.8372	Intermediate Similarity	NPC475022
0.8372	Intermediate Similarity	NPC186975
0.8372	Intermediate Similarity	NPC325594
0.8372	Intermediate Similarity	NPC72133

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 NPC165064 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	133
0.1-0.2	1330
0.2-0.3	3973
0.3-0.4	2483
0.4-0.5	681
0.5-0.6	219
0.6-0.7	160
0.7-0.8	161
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8795	High Similarity	NPD4786	Approved
0.8554	High Similarity	NPD3667	Approved
0.8427	Intermediate Similarity	NPD6399	Phase 3
0.8353	Intermediate Similarity	NPD3665	Phase 1
0.8353	Intermediate Similarity	NPD3666	Approved
0.8353	Intermediate Similarity	NPD3133	Approved
0.8295	Intermediate Similarity	NPD5328	Approved
0.8293	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD7334	Approved
0.8161	Intermediate Similarity	NPD5279	Phase 3
0.8161	Intermediate Similarity	NPD7521	Approved
0.8161	Intermediate Similarity	NPD5330	Approved
0.8161	Intermediate Similarity	NPD7146	Approved
0.8161	Intermediate Similarity	NPD6409	Approved
0.8161	Intermediate Similarity	NPD6684	Approved
0.8161	Intermediate Similarity	NPD3618	Phase 1
0.8111	Intermediate Similarity	NPD6079	Approved
0.8065	Intermediate Similarity	NPD6083	Phase 2
0.8065	Intermediate Similarity	NPD6084	Phase 2
0.7978	Intermediate Similarity	NPD5737	Approved
0.7978	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD6672	Approved
0.7978	Intermediate Similarity	NPD6903	Approved
0.7927	Intermediate Similarity	NPD6942	Approved
0.7927	Intermediate Similarity	NPD7339	Approved
0.7912	Intermediate Similarity	NPD7515	Phase 2
0.7907	Intermediate Similarity	NPD4223	Phase 3
0.7907	Intermediate Similarity	NPD4221	Approved
0.7889	Intermediate Similarity	NPD4753	Phase 2
0.7849	Intermediate Similarity	NPD5695	Phase 3
0.7841	Intermediate Similarity	NPD5329	Approved
0.7826	Intermediate Similarity	NPD4202	Approved
0.7816	Intermediate Similarity	NPD5362	Discontinued
0.7753	Intermediate Similarity	NPD6098	Approved
0.7727	Intermediate Similarity	NPD3668	Phase 3
0.7727	Intermediate Similarity	NPD4197	Approved
0.7717	Intermediate Similarity	NPD5281	Approved
0.7717	Intermediate Similarity	NPD5284	Approved
0.7708	Intermediate Similarity	NPD7640	Approved
0.7708	Intermediate Similarity	NPD7639	Approved
0.7677	Intermediate Similarity	NPD6675	Approved
0.7677	Intermediate Similarity	NPD5739	Approved
0.7677	Intermediate Similarity	NPD6402	Approved
0.7677	Intermediate Similarity	NPD7128	Approved
0.7619	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD4788	Approved
0.7604	Intermediate Similarity	NPD5696	Approved
0.7604	Intermediate Similarity	NPD7638	Approved
0.759	Intermediate Similarity	NPD6924	Approved
0.759	Intermediate Similarity	NPD6926	Approved
0.759	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD5221	Approved
0.7579	Intermediate Similarity	NPD5222	Approved
0.7579	Intermediate Similarity	NPD4697	Phase 3
0.7579	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6929	Approved
0.7556	Intermediate Similarity	NPD4688	Approved
0.7556	Intermediate Similarity	NPD4138	Approved
0.7556	Intermediate Similarity	NPD5690	Phase 2
0.7556	Intermediate Similarity	NPD4689	Approved
0.7556	Intermediate Similarity	NPD4690	Approved
0.7556	Intermediate Similarity	NPD5280	Approved
0.7556	Intermediate Similarity	NPD4693	Phase 3
0.7556	Intermediate Similarity	NPD5205	Approved
0.7556	Intermediate Similarity	NPD4694	Approved
0.7553	Intermediate Similarity	NPD7748	Approved
0.7551	Intermediate Similarity	NPD5211	Phase 2
0.7527	Intermediate Similarity	NPD8034	Phase 2
0.7527	Intermediate Similarity	NPD7637	Suspended
0.7527	Intermediate Similarity	NPD8035	Phase 2
0.7526	Intermediate Similarity	NPD6404	Discontinued
0.7525	Intermediate Similarity	NPD7320	Approved
0.7525	Intermediate Similarity	NPD6899	Approved
0.7525	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD6904	Approved
0.75	Intermediate Similarity	NPD4269	Approved
0.75	Intermediate Similarity	NPD4270	Approved
0.75	Intermediate Similarity	NPD5173	Approved
0.75	Intermediate Similarity	NPD6080	Approved
0.75	Intermediate Similarity	NPD6673	Approved
0.75	Intermediate Similarity	NPD4755	Approved
0.7474	Intermediate Similarity	NPD4629	Approved
0.7474	Intermediate Similarity	NPD5210	Approved
0.7471	Intermediate Similarity	NPD6931	Approved
0.7471	Intermediate Similarity	NPD7525	Registered
0.7471	Intermediate Similarity	NPD6930	Phase 2
0.7451	Intermediate Similarity	NPD6372	Approved
0.7451	Intermediate Similarity	NPD6373	Approved
0.7442	Intermediate Similarity	NPD3617	Approved
0.7426	Intermediate Similarity	NPD5697	Approved
0.7426	Intermediate Similarity	NPD5701	Approved
0.7416	Intermediate Similarity	NPD5331	Approved
0.7416	Intermediate Similarity	NPD5332	Approved
0.7412	Intermediate Similarity	NPD6933	Approved
0.7412	Intermediate Similarity	NPD6117	Approved
0.74	Intermediate Similarity	NPD5141	Approved
0.7391	Intermediate Similarity	NPD5208	Approved
0.7386	Intermediate Similarity	NPD4790	Discontinued
0.7386	Intermediate Similarity	NPD4692	Approved
0.7386	Intermediate Similarity	NPD4139	Approved
0.7379	Intermediate Similarity	NPD7290	Approved
0.7379	Intermediate Similarity	NPD7102	Approved
0.7379	Intermediate Similarity	NPD6883	Approved
0.7363	Intermediate Similarity	NPD4623	Approved
0.7363	Intermediate Similarity	NPD4519	Discontinued
0.7353	Intermediate Similarity	NPD6011	Approved
0.7349	Intermediate Similarity	NPD4243	Approved
0.7347	Intermediate Similarity	NPD5286	Approved
0.7347	Intermediate Similarity	NPD4700	Approved
0.7347	Intermediate Similarity	NPD4696	Approved
0.7347	Intermediate Similarity	NPD5285	Approved
0.734	Intermediate Similarity	NPD5693	Phase 1
0.734	Intermediate Similarity	NPD6050	Approved
0.734	Intermediate Similarity	NPD6411	Approved
0.7326	Intermediate Similarity	NPD5776	Phase 2
0.7326	Intermediate Similarity	NPD6925	Approved
0.7326	Intermediate Similarity	NPD6116	Phase 1
0.732	Intermediate Similarity	NPD7902	Approved
0.7317	Intermediate Similarity	NPD6923	Approved
0.7317	Intermediate Similarity	NPD6922	Approved
0.7312	Intermediate Similarity	NPD6051	Approved
0.7308	Intermediate Similarity	NPD6869	Approved
0.7308	Intermediate Similarity	NPD6650	Approved
0.7308	Intermediate Similarity	NPD6847	Approved
0.7308	Intermediate Similarity	NPD6649	Approved
0.7308	Intermediate Similarity	NPD8130	Phase 1
0.7308	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6617	Approved
0.7303	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7115	Discovery
0.7283	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6014	Approved
0.7282	Intermediate Similarity	NPD6013	Approved
0.7282	Intermediate Similarity	NPD6012	Approved
0.7273	Intermediate Similarity	NPD4252	Approved
0.7273	Intermediate Similarity	NPD4819	Approved
0.7273	Intermediate Similarity	NPD4821	Approved
0.7273	Intermediate Similarity	NPD4822	Approved
0.7273	Intermediate Similarity	NPD5368	Approved
0.7273	Intermediate Similarity	NPD5223	Approved
0.7273	Intermediate Similarity	NPD4820	Approved
0.7263	Intermediate Similarity	NPD5778	Approved
0.7263	Intermediate Similarity	NPD5779	Approved
0.7253	Intermediate Similarity	NPD5363	Approved
0.725	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6115	Approved
0.7241	Intermediate Similarity	NPD6114	Approved
0.7241	Intermediate Similarity	NPD6697	Approved
0.7241	Intermediate Similarity	NPD4271	Approved
0.7241	Intermediate Similarity	NPD7145	Approved
0.7241	Intermediate Similarity	NPD6118	Approved
0.7241	Intermediate Similarity	NPD4268	Approved
0.7238	Intermediate Similarity	NPD6882	Approved
0.7238	Intermediate Similarity	NPD8297	Approved
0.7234	Intermediate Similarity	NPD5785	Approved
0.7234	Intermediate Similarity	NPD5692	Phase 3
0.7234	Intermediate Similarity	NPD5207	Approved
0.7229	Intermediate Similarity	NPD4747	Approved
0.7229	Intermediate Similarity	NPD7144	Approved
0.7229	Intermediate Similarity	NPD7143	Approved
0.7222	Intermediate Similarity	NPD7154	Phase 3
0.7222	Intermediate Similarity	NPD6695	Phase 3
0.72	Intermediate Similarity	NPD5225	Approved
0.72	Intermediate Similarity	NPD4633	Approved
0.72	Intermediate Similarity	NPD5226	Approved
0.72	Intermediate Similarity	NPD5224	Approved
0.7191	Intermediate Similarity	NPD5369	Approved
0.7176	Intermediate Similarity	NPD4785	Approved
0.7176	Intermediate Similarity	NPD4784	Approved
0.7176	Intermediate Similarity	NPD5733	Approved
0.7174	Intermediate Similarity	NPD5786	Approved
0.7174	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4195	Approved
0.7158	Intermediate Similarity	NPD5694	Approved
0.7143	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7150	Approved
0.7143	Intermediate Similarity	NPD7152	Approved
0.7143	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7151	Approved
0.7129	Intermediate Similarity	NPD4754	Approved
0.7129	Intermediate Similarity	NPD5175	Approved
0.7129	Intermediate Similarity	NPD5174	Approved
0.7128	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6101	Approved
0.7128	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6435	Approved
0.7108	Intermediate Similarity	NPD4137	Phase 3
0.7087	Intermediate Similarity	NPD6412	Phase 2
0.7079	Intermediate Similarity	NPD7514	Phase 3
0.7079	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4695	Discontinued
0.7065	Intermediate Similarity	NPD1694	Approved
0.7065	Intermediate Similarity	NPD6893	Approved
0.7053	Intermediate Similarity	NPD4096	Approved
0.7045	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6868	Approved
0.703	Intermediate Similarity	NPD7632	Discontinued

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