NPASS Compound

Structure

NPC472869 OpenBabel07101719252D 35 37 0 0 1 0 0 0 0 0999 V2000 -5.9975 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5955 -2.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3994 -2.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2103 1.6059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2967 2.0126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9401 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9975 -2.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1314 -2.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8635 -2.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1756 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1810 1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2654 0.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0181 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3994 0.8955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1314 -1.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7295 -2.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3994 -1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2654 -0.6045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5823 0.7045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5334 -0.6045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9316 -1.8080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7295 -3.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 1.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5334 0.3955 0.0000 C 0 0 2 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 2.7406 -1.2202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0361 -2.8025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5955 -4.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8635 -4.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 0.2091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 18 1 0 0 0 0 10 19 2 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 25 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 23 1 0 0 0 0 17 24 2 0 0 0 0 18 1 1 1 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 21 18 1 1 0 0 0 22 24 1 0 0 0 0 22 29 1 6 0 0 0 23 29 1 1 0 0 0 24 30 1 0 0 0 0 25 28 1 0 0 0 0 25 30 1 1 0 0 0 26 31 2 0 0 0 0 26 32 1 0 0 0 0 27 33 2 0 0 0 0 27 34 1 0 0 0 0 28 35 1 0 0 0 0 29 6 1 6 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	532.535
LogP:	5.398
LogD:	3.798
LogS:	-3.632
# Rotatable Bonds:	9
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.324
Synthetic Accessibility Score:	5.379
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.873
MDCK Permeability:	1.0005260264733806e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.029
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.106
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.082
Plasma Protein Binding (PPB):	95.50618743896484%
Volume Distribution (VD):	0.423
Pgp-substrate:	6.348574161529541%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.155
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.896
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.071
CYP3A4-substrate:	0.066

ADMET: Excretion

Clearance (CL):	1.269
Half-life (T1/2):	0.736

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.261
Drug-inuced Liver Injury (DILI):	0.104
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.506
Maximum Recommended Daily Dose:	0.275
Skin Sensitization:	0.093
Carcinogencity:	0.166
Eye Corrosion:	0.007
Eye Irritation:	0.025
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC472869

Natural Product ID:	NPC472869
*Common Name:**	SCRHXYJKBNGZOH-HGIOFNIASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SCRHXYJKBNGZOH-HGIOFNIASA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-18(9-8-10-19(2)27(33)34)21-13-15-29(6)22-11-12-25(28(4,5)35)30(7,16-14-26(31)32)24(22)17-23(29)20(21)3/h10,17-18,21-23,25,35H,3,8-9,11-16H2,1-2,4-7H3,(H,31,32)(H,33,34)/b19-10-/t18-,21-,22-,23+,25+,29+,30-/m1/s1
SMILES:	OC(=O)CC[C@]1(C)C2=C[C@@H]3[C@@]([C@@H]2CC[C@H]1C(O)(C)C)(C)CC[C@@H](C3=C)[C@@H](CC/C=C(C(=O)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593375
PubChem CID:	n.a.
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
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
EC50	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	143400.0	nM	PMID[491531]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	58700.0	nM	PMID[491531]
NPT27	Others	Unspecified		Ratio CC50/EC50	=	2.4	n.a.	PMID[491531]

☑ 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 NPC472869 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	163
0.1-0.2	1048
0.2-0.3	4657
0.3-0.4	13252
0.4-0.5	9833
0.5-0.6	7265
0.6-0.7	4670
0.7-0.8	1601
0.8-0.85	155
0.85-0.9	38
0.9-0.95	11
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9756	High Similarity	NPC472870
0.975	High Similarity	NPC19849
0.975	High Similarity	NPC472864
0.9524	High Similarity	NPC472866
0.9518	High Similarity	NPC117122
0.9506	High Similarity	NPC472865
0.9302	High Similarity	NPC472871
0.9277	High Similarity	NPC186975
0.9268	High Similarity	NPC248758
0.9268	High Similarity	NPC164577
0.9176	High Similarity	NPC262043
0.9167	High Similarity	NPC136948
0.9167	High Similarity	NPC236618
0.9157	High Similarity	NPC269638
0.9146	High Similarity	NPC97913
0.9	High Similarity	NPC198240
0.8953	High Similarity	NPC66344
0.8941	High Similarity	NPC128644
0.8875	High Similarity	NPC61952
0.8795	High Similarity	NPC472867
0.875	High Similarity	NPC474018
0.875	High Similarity	NPC473986
0.875	High Similarity	NPC204341
0.875	High Similarity	NPC470113
0.8721	High Similarity	NPC476409
0.8706	High Similarity	NPC29447
0.8696	High Similarity	NPC470074
0.8675	High Similarity	NPC278459
0.8675	High Similarity	NPC477372
0.8667	High Similarity	NPC476174
0.8621	High Similarity	NPC48107
0.8571	High Similarity	NPC29152
0.8571	High Similarity	NPC320514
0.8571	High Similarity	NPC472239
0.8539	High Similarity	NPC476187
0.8537	High Similarity	NPC179028
0.8488	Intermediate Similarity	NPC60350
0.8478	Intermediate Similarity	NPC476253
0.8478	Intermediate Similarity	NPC156546
0.8471	Intermediate Similarity	NPC279639
0.8471	Intermediate Similarity	NPC49019
0.8471	Intermediate Similarity	NPC215893
0.8471	Intermediate Similarity	NPC310470
0.8471	Intermediate Similarity	NPC167103
0.8471	Intermediate Similarity	NPC3856
0.8471	Intermediate Similarity	NPC477373
0.8462	Intermediate Similarity	NPC293052
0.8452	Intermediate Similarity	NPC147066
0.8452	Intermediate Similarity	NPC40228
0.8434	Intermediate Similarity	NPC477371
0.8434	Intermediate Similarity	NPC158846
0.8415	Intermediate Similarity	NPC132542
0.8415	Intermediate Similarity	NPC97377
0.8409	Intermediate Similarity	NPC72397
0.8409	Intermediate Similarity	NPC104560
0.8404	Intermediate Similarity	NPC118174
0.8395	Intermediate Similarity	NPC476795
0.8372	Intermediate Similarity	NPC16287
0.8372	Intermediate Similarity	NPC165064
0.8372	Intermediate Similarity	NPC178025
0.8372	Intermediate Similarity	NPC476038
0.8372	Intermediate Similarity	NPC181743
0.8372	Intermediate Similarity	NPC194937
0.837	Intermediate Similarity	NPC456
0.837	Intermediate Similarity	NPC301534
0.837	Intermediate Similarity	NPC472941
0.837	Intermediate Similarity	NPC250757
0.837	Intermediate Similarity	NPC235053
0.8353	Intermediate Similarity	NPC3511
0.8353	Intermediate Similarity	NPC133391
0.8353	Intermediate Similarity	NPC142253
0.8353	Intermediate Similarity	NPC469804
0.8353	Intermediate Similarity	NPC469806
0.8353	Intermediate Similarity	NPC469799
0.8353	Intermediate Similarity	NPC469805
0.8333	Intermediate Similarity	NPC37038
0.8333	Intermediate Similarity	NPC472868
0.8315	Intermediate Similarity	NPC174342
0.8315	Intermediate Similarity	NPC214387
0.8313	Intermediate Similarity	NPC275494
0.8313	Intermediate Similarity	NPC471409
0.8313	Intermediate Similarity	NPC74410
0.8313	Intermediate Similarity	NPC239098
0.8313	Intermediate Similarity	NPC321514
0.8298	Intermediate Similarity	NPC471041
0.8293	Intermediate Similarity	NPC180886
0.8276	Intermediate Similarity	NPC65661
0.8276	Intermediate Similarity	NPC142649
0.8276	Intermediate Similarity	NPC283733
0.8276	Intermediate Similarity	NPC8571
0.8272	Intermediate Similarity	NPC18819
0.8272	Intermediate Similarity	NPC46610
0.8261	Intermediate Similarity	NPC171395
0.8256	Intermediate Similarity	NPC470015
0.8256	Intermediate Similarity	NPC472740
0.8256	Intermediate Similarity	NPC168188
0.8242	Intermediate Similarity	NPC476416
0.8235	Intermediate Similarity	NPC471898
0.8235	Intermediate Similarity	NPC90055
0.8235	Intermediate Similarity	NPC201912
0.8235	Intermediate Similarity	NPC38350
0.8222	Intermediate Similarity	NPC476369
0.8222	Intermediate Similarity	NPC476437
0.8222	Intermediate Similarity	NPC477147
0.8222	Intermediate Similarity	NPC477149
0.8214	Intermediate Similarity	NPC231431
0.8214	Intermediate Similarity	NPC215843
0.8211	Intermediate Similarity	NPC282524
0.8193	Intermediate Similarity	NPC66105
0.8193	Intermediate Similarity	NPC165711
0.8191	Intermediate Similarity	NPC197386
0.8191	Intermediate Similarity	NPC235464
0.8191	Intermediate Similarity	NPC471717
0.8191	Intermediate Similarity	NPC166745
0.8191	Intermediate Similarity	NPC98868
0.8171	Intermediate Similarity	NPC469803
0.8171	Intermediate Similarity	NPC39362
0.8161	Intermediate Similarity	NPC476412
0.8161	Intermediate Similarity	NPC96095
0.8161	Intermediate Similarity	NPC87552
0.8152	Intermediate Similarity	NPC8993
0.8152	Intermediate Similarity	NPC299100
0.8148	Intermediate Similarity	NPC35656
0.814	Intermediate Similarity	NPC260956
0.814	Intermediate Similarity	NPC193347
0.814	Intermediate Similarity	NPC2524
0.8132	Intermediate Similarity	NPC473998
0.8132	Intermediate Similarity	NPC475806
0.8132	Intermediate Similarity	NPC289479
0.8125	Intermediate Similarity	NPC235586
0.8118	Intermediate Similarity	NPC469797
0.8118	Intermediate Similarity	NPC469798
0.8111	Intermediate Similarity	NPC118011
0.8111	Intermediate Similarity	NPC262858
0.8111	Intermediate Similarity	NPC5509
0.8111	Intermediate Similarity	NPC36668
0.8111	Intermediate Similarity	NPC146554
0.8111	Intermediate Similarity	NPC309603
0.8111	Intermediate Similarity	NPC310236
0.8111	Intermediate Similarity	NPC472240
0.8111	Intermediate Similarity	NPC473999
0.8105	Intermediate Similarity	NPC476274
0.8105	Intermediate Similarity	NPC241221
0.8105	Intermediate Similarity	NPC287833
0.8095	Intermediate Similarity	NPC280654
0.8095	Intermediate Similarity	NPC260385
0.8095	Intermediate Similarity	NPC321690
0.8095	Intermediate Similarity	NPC169095
0.8095	Intermediate Similarity	NPC59436
0.8095	Intermediate Similarity	NPC110094
0.809	Intermediate Similarity	NPC476293
0.809	Intermediate Similarity	NPC96496
0.8085	Intermediate Similarity	NPC107243
0.8085	Intermediate Similarity	NPC253826
0.8072	Intermediate Similarity	NPC246445
0.8068	Intermediate Similarity	NPC86316
0.8068	Intermediate Similarity	NPC474537
0.8068	Intermediate Similarity	NPC106416
0.8068	Intermediate Similarity	NPC94531
0.8068	Intermediate Similarity	NPC471224
0.8068	Intermediate Similarity	NPC311702
0.8068	Intermediate Similarity	NPC123319
0.8065	Intermediate Similarity	NPC469995
0.8065	Intermediate Similarity	NPC173875
0.8065	Intermediate Similarity	NPC180950
0.8065	Intermediate Similarity	NPC318282
0.8065	Intermediate Similarity	NPC174948
0.8046	Intermediate Similarity	NPC105803
0.8046	Intermediate Similarity	NPC69279
0.8046	Intermediate Similarity	NPC477852
0.8046	Intermediate Similarity	NPC476927
0.8046	Intermediate Similarity	NPC83569
0.8043	Intermediate Similarity	NPC151722
0.8043	Intermediate Similarity	NPC38232
0.8043	Intermediate Similarity	NPC476304
0.8043	Intermediate Similarity	NPC474736
0.8043	Intermediate Similarity	NPC472303
0.8041	Intermediate Similarity	NPC72151
0.8041	Intermediate Similarity	NPC112009
0.8041	Intermediate Similarity	NPC180204
0.8025	Intermediate Similarity	NPC21944
0.8025	Intermediate Similarity	NPC160817
0.8025	Intermediate Similarity	NPC133253
0.8023	Intermediate Similarity	NPC327002
0.8023	Intermediate Similarity	NPC232625
0.8023	Intermediate Similarity	NPC473217
0.8023	Intermediate Similarity	NPC14203
0.8023	Intermediate Similarity	NPC229584
0.8023	Intermediate Similarity	NPC142244
0.8022	Intermediate Similarity	NPC48010
0.8022	Intermediate Similarity	NPC469400
0.8022	Intermediate Similarity	NPC51486
0.8021	Intermediate Similarity	NPC472924
0.8021	Intermediate Similarity	NPC224720
0.8021	Intermediate Similarity	NPC476240
0.8021	Intermediate Similarity	NPC476223
0.8021	Intermediate Similarity	NPC99411
0.8	Intermediate Similarity	NPC199595
0.8	Intermediate Similarity	NPC194196
0.8	Intermediate Similarity	NPC196827

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 NPC472869 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	1385
0.2-0.3	3757
0.3-0.4	2546
0.4-0.5	798
0.5-0.6	238
0.6-0.7	189
0.7-0.8	78
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8182	Intermediate Similarity	NPD4623	Approved
0.8182	Intermediate Similarity	NPD4519	Discontinued
0.814	Intermediate Similarity	NPD4221	Approved
0.814	Intermediate Similarity	NPD4223	Phase 3
0.8068	Intermediate Similarity	NPD5329	Approved
0.7955	Intermediate Similarity	NPD4197	Approved
0.7935	Intermediate Similarity	NPD5284	Approved
0.7935	Intermediate Similarity	NPD5281	Approved
0.7931	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD6080	Approved
0.7912	Intermediate Similarity	NPD6904	Approved
0.7912	Intermediate Similarity	NPD6673	Approved
0.7895	Intermediate Similarity	NPD6084	Phase 2
0.7895	Intermediate Similarity	NPD6083	Phase 2
0.7802	Intermediate Similarity	NPD5737	Approved
0.7802	Intermediate Similarity	NPD6672	Approved
0.7778	Intermediate Similarity	NPD4138	Approved
0.7778	Intermediate Similarity	NPD4688	Approved
0.7778	Intermediate Similarity	NPD5690	Phase 2
0.7778	Intermediate Similarity	NPD5205	Approved
0.7778	Intermediate Similarity	NPD4690	Approved
0.7778	Intermediate Similarity	NPD4693	Phase 3
0.7778	Intermediate Similarity	NPD4689	Approved
0.7778	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5693	Phase 1
0.7732	Intermediate Similarity	NPD6404	Discontinued
0.7717	Intermediate Similarity	NPD4753	Phase 2
0.7701	Intermediate Similarity	NPD4695	Discontinued
0.7684	Intermediate Similarity	NPD5695	Phase 3
0.766	Intermediate Similarity	NPD6399	Phase 3
0.7629	Intermediate Similarity	NPD5696	Approved
0.7609	Intermediate Similarity	NPD5208	Approved
0.7586	Intermediate Similarity	NPD4195	Approved
0.7582	Intermediate Similarity	NPD5330	Approved
0.7582	Intermediate Similarity	NPD6409	Approved
0.7582	Intermediate Similarity	NPD6684	Approved
0.7582	Intermediate Similarity	NPD6098	Approved
0.7582	Intermediate Similarity	NPD7521	Approved
0.7582	Intermediate Similarity	NPD7334	Approved
0.7582	Intermediate Similarity	NPD7146	Approved
0.7582	Intermediate Similarity	NPD4694	Approved
0.7582	Intermediate Similarity	NPD5280	Approved
0.7556	Intermediate Similarity	NPD4786	Approved
0.7556	Intermediate Similarity	NPD3665	Phase 1
0.7556	Intermediate Similarity	NPD3666	Approved
0.7556	Intermediate Similarity	NPD3133	Approved
0.7553	Intermediate Similarity	NPD6050	Approved
0.7553	Intermediate Similarity	NPD6079	Approved
0.7553	Intermediate Similarity	NPD7515	Phase 2
0.7551	Intermediate Similarity	NPD7639	Approved
0.7551	Intermediate Similarity	NPD7640	Approved
0.7527	Intermediate Similarity	NPD5328	Approved
0.7527	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4629	Approved
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5210	Approved
0.7471	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3617	Approved
0.7449	Intermediate Similarity	NPD7638	Approved
0.7447	Intermediate Similarity	NPD5692	Phase 3
0.7444	Intermediate Similarity	NPD4788	Approved
0.7419	Intermediate Similarity	NPD6903	Approved
0.7419	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5211	Phase 2
0.7396	Intermediate Similarity	NPD7748	Approved
0.7391	Intermediate Similarity	NPD3618	Phase 1
0.7379	Intermediate Similarity	NPD6881	Approved
0.7379	Intermediate Similarity	NPD6899	Approved
0.7368	Intermediate Similarity	NPD5694	Approved
0.7353	Intermediate Similarity	NPD6675	Approved
0.7353	Intermediate Similarity	NPD6402	Approved
0.7353	Intermediate Similarity	NPD7128	Approved
0.7353	Intermediate Similarity	NPD5739	Approved
0.7333	Intermediate Similarity	NPD3667	Approved
0.7315	Intermediate Similarity	NPD7115	Discovery
0.7312	Intermediate Similarity	NPD3573	Approved
0.7292	Intermediate Similarity	NPD4202	Approved
0.7283	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5697	Approved
0.7263	Intermediate Similarity	NPD5207	Approved
0.7262	Intermediate Similarity	NPD4691	Approved
0.7262	Intermediate Similarity	NPD4747	Approved
0.7255	Intermediate Similarity	NPD5141	Approved
0.7253	Intermediate Similarity	NPD5362	Discontinued
0.7245	Intermediate Similarity	NPD5222	Approved
0.7245	Intermediate Similarity	NPD5221	Approved
0.7245	Intermediate Similarity	NPD7614	Phase 1
0.7245	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7102	Approved
0.7238	Intermediate Similarity	NPD6883	Approved
0.7238	Intermediate Similarity	NPD7290	Approved
0.7216	Intermediate Similarity	NPD6001	Approved
0.7212	Intermediate Similarity	NPD6011	Approved
0.7212	Intermediate Similarity	NPD7320	Approved
0.7204	Intermediate Similarity	NPD5279	Phase 3
0.72	Intermediate Similarity	NPD5286	Approved
0.72	Intermediate Similarity	NPD4696	Approved
0.72	Intermediate Similarity	NPD5285	Approved
0.7176	Intermediate Similarity	NPD4243	Approved
0.7172	Intermediate Similarity	NPD4755	Approved
0.7172	Intermediate Similarity	NPD7902	Approved
0.7172	Intermediate Similarity	NPD5173	Approved
0.717	Intermediate Similarity	NPD6869	Approved
0.717	Intermediate Similarity	NPD6617	Approved
0.717	Intermediate Similarity	NPD8130	Phase 1
0.717	Intermediate Similarity	NPD6650	Approved
0.717	Intermediate Similarity	NPD6649	Approved
0.717	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD6373	Approved
0.7143	Intermediate Similarity	NPD6012	Approved
0.7143	Intermediate Similarity	NPD6372	Approved
0.7143	Intermediate Similarity	NPD6014	Approved
0.7143	Intermediate Similarity	NPD6013	Approved
0.7143	Intermediate Similarity	NPD4137	Phase 3
0.7129	Intermediate Similarity	NPD5223	Approved
0.7115	Intermediate Similarity	NPD5701	Approved
0.7103	Intermediate Similarity	NPD8297	Approved
0.7103	Intermediate Similarity	NPD6882	Approved
0.71	Intermediate Similarity	NPD4225	Approved
0.7097	Intermediate Similarity	NPD5363	Approved
0.7083	Intermediate Similarity	NPD4096	Approved
0.7083	Intermediate Similarity	NPD5785	Approved
0.7071	Intermediate Similarity	NPD4697	Phase 3
0.7059	Intermediate Similarity	NPD5091	Approved
0.7059	Intermediate Similarity	NPD5225	Approved
0.7059	Intermediate Similarity	NPD5226	Approved
0.7059	Intermediate Similarity	NPD5224	Approved
0.7059	Intermediate Similarity	NPD4633	Approved
0.7048	Intermediate Similarity	NPD6686	Approved
0.7033	Intermediate Similarity	NPD4139	Approved
0.7033	Intermediate Similarity	NPD4692	Approved
0.703	Intermediate Similarity	NPD4700	Approved
0.7011	Intermediate Similarity	NPD4784	Approved
0.7011	Intermediate Similarity	NPD5733	Approved
0.7011	Intermediate Similarity	NPD4785	Approved
0.7011	Intermediate Similarity	NPD4058	Approved
0.701	Intermediate Similarity	NPD7637	Suspended
0.701	Intermediate Similarity	NPD8035	Phase 2
0.701	Intermediate Similarity	NPD8034	Phase 2
0.7009	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5175	Approved
0.699	Remote Similarity	NPD5174	Approved
0.699	Remote Similarity	NPD6052	Approved
0.6989	Remote Similarity	NPD3668	Phase 3
0.6979	Remote Similarity	NPD6051	Approved
0.6977	Remote Similarity	NPD6081	Approved
0.697	Remote Similarity	NPD5654	Approved
0.6952	Remote Similarity	NPD6614	Approved
0.6939	Remote Similarity	NPD5133	Approved
0.6923	Remote Similarity	NPD7525	Registered
0.6915	Remote Similarity	NPD1694	Approved
0.6893	Remote Similarity	NPD7632	Discontinued
0.6889	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7154	Phase 3
0.6881	Remote Similarity	NPD4632	Approved
0.6875	Remote Similarity	NPD4518	Approved
0.6869	Remote Similarity	NPD7900	Approved
0.6869	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5959	Approved
0.6827	Remote Similarity	NPD4754	Approved
0.6818	Remote Similarity	NPD4687	Approved
0.6818	Remote Similarity	NPD6926	Approved
0.6818	Remote Similarity	NPD6924	Approved
0.6786	Remote Similarity	NPD6335	Approved
0.6786	Remote Similarity	NPD4224	Phase 2
0.6786	Remote Similarity	NPD7331	Phase 2
0.6782	Remote Similarity	NPD5276	Approved
0.6774	Remote Similarity	NPD4270	Approved
0.6774	Remote Similarity	NPD4269	Approved
0.6757	Remote Similarity	NPD6274	Approved
0.6757	Remote Similarity	NPD6868	Approved
0.6742	Remote Similarity	NPD7339	Approved
0.6742	Remote Similarity	NPD5275	Approved
0.6742	Remote Similarity	NPD4190	Phase 3
0.6742	Remote Similarity	NPD6942	Approved
0.6739	Remote Similarity	NPD7332	Phase 2
0.6739	Remote Similarity	NPD4819	Approved
0.6739	Remote Similarity	NPD6930	Phase 2
0.6739	Remote Similarity	NPD4821	Approved
0.6739	Remote Similarity	NPD4822	Approved
0.6739	Remote Similarity	NPD4820	Approved
0.6739	Remote Similarity	NPD6931	Approved
0.6737	Remote Similarity	NPD1696	Phase 3
0.6733	Remote Similarity	NPD7732	Phase 3
0.6729	Remote Similarity	NPD4730	Approved
0.6729	Remote Similarity	NPD4729	Approved
0.6729	Remote Similarity	NPD5128	Approved
0.6726	Remote Similarity	NPD7100	Approved
0.6726	Remote Similarity	NPD7101	Approved
0.6702	Remote Similarity	NPD5331	Approved
0.6702	Remote Similarity	NPD6695	Phase 3
0.6702	Remote Similarity	NPD5332	Approved
0.6698	Remote Similarity	NPD6008	Approved
0.6698	Remote Similarity	NPD4767	Approved
0.6698	Remote Similarity	NPD4768	Approved
0.6696	Remote Similarity	NPD6317	Approved
0.6696	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD4790	Discontinued
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD6933	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