NPASS Compound

Structure

NPC471234 OpenBabel07101719142D 39 44 0 0 1 0 0 0 0 0999 V2000 -1.3276 0.5911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9023 -0.1999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1519 -3.0274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0450 -1.5821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9023 -0.1999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5351 -4.0337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3514 -2.5599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0514 -3.9838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1982 -2.0710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7780 -3.3295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9940 -2.0656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8918 -1.0932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5046 -2.0710 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8785 -3.6816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9504 -2.2689 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.0450 -0.6043 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3514 0.3735 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7850 -0.6955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1982 0.8624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9299 -1.2799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9299 -0.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5747 -2.3731 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1982 -1.0932 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5046 -1.0932 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.5821 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3514 -0.6043 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5747 -0.7910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0818 -2.7252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3481 -3.1621 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9883 0.2609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1982 1.8401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7210 -1.8547 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5747 -2.3731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7242 0.7910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6052 -4.3359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4393 -1.4221 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0450 0.3735 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5046 -0.1154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 35 1 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 2 0 0 0 0 8 14 1 0 0 0 0 9 23 1 0 0 0 0 10 22 1 0 0 0 0 11 12 2 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 22 1 6 0 0 0 13 24 1 0 0 0 0 14 28 2 0 0 0 0 14 35 1 0 0 0 0 15 29 1 0 0 0 0 15 36 1 0 0 0 0 16 23 1 1 0 0 0 16 37 1 0 0 0 0 17 19 1 0 0 0 0 17 26 1 1 0 0 0 17 38 1 0 0 0 0 18 30 2 0 0 0 0 18 36 1 0 0 0 0 19 31 2 0 0 0 0 19 37 1 0 0 0 0 20 21 1 0 0 0 0 20 25 1 0 0 0 0 20 32 2 0 0 0 0 21 39 1 0 0 0 0 22 25 1 1 0 0 0 23 26 1 1 0 0 0 24 26 1 1 0 0 0 25 27 1 6 0 0 0 25 33 1 0 0 0 0 26 38 1 6 0 0 0 27 24 1 1 0 0 0 27 34 1 0 0 0 0 27 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	548.19
Volume:	513.873
LogP:	2.409
LogD:	1.131
LogS:	-4.338
# Rotatable Bonds:	4
TPSA:	185.49
# H-Bond Aceptor:	12
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.242
Synthetic Accessibility Score:	6.305
Fsp3:	0.667
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.828
MDCK Permeability:	2.6480311134946533e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.926
Human Intestinal Absorption (HIA):	0.682
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.988
Plasma Protein Binding (PPB):	74.55718231201172%
Volume Distribution (VD):	0.563
Pgp-substrate:	30.04039192199707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.977
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.429
CYP2C9-inhibitor:	0.071
CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.184
CYP3A4-substrate:	0.627

ADMET: Excretion

Clearance (CL):	4.713
Half-life (T1/2):	0.521

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.473
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.822
Rat Oral Acute Toxicity:	0.946
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.13
Carcinogencity:	0.94
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.867

Download Data

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

Natural Product: NPC471234

Natural Product ID:	NPC471234
*Common Name:**	Harperfolide
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FBSDZWINUANERE-SYFIMXEOSA-N
Standard InCHI:	InChI=1S/C27H32O12/c1-21(2)20(32)25(33)22(3,10-8-14(28)35-6)13-7-9-23(4)16(12-11-15(29)36-18(12)30)37-19(31)17-26(23,38-17)24(13,5)27(25,34)39-21/h8,10-11,13,15-17,29,33-34H,7,9H2,1-6H3/b10-8-/t13-,15?,16+,17-,22-,23+,24-,25+,26-,27+/m1/s1
SMILES:	COC(=O)/C=C[C@]1(C)[C@H]2CC[C@@]3([C@]4([C@@]2([C@]2([C@]1(O)C(=O)C(O2)(C)C)O)C)O[C@@H]4C(=O)O[C@H]3C1=CC(OC1=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2398514
PubChem CID:	72714904
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	root	n.a.	PMID[16394547]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23688954]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21362	Harrisonia perforata	Species	Rutaceae	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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6510.0	nM	PMID[510602]

☑ 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 NPC471234 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	296
0.1-0.2	1604
0.2-0.3	4746
0.3-0.4	8069
0.4-0.5	12609
0.5-0.6	7548
0.6-0.7	5787
0.7-0.8	1873
0.8-0.85	145
0.85-0.9	19
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8815	High Similarity	NPC194854
0.8815	High Similarity	NPC48813
0.875	High Similarity	NPC16729
0.875	High Similarity	NPC475462
0.8741	High Similarity	NPC471172
0.8682	High Similarity	NPC476852
0.8672	High Similarity	NPC311534
0.8672	High Similarity	NPC473620
0.8629	High Similarity	NPC19028
0.8629	High Similarity	NPC9674
0.8605	High Similarity	NPC470880
0.8605	High Similarity	NPC175186
0.8605	High Similarity	NPC476851
0.8605	High Similarity	NPC104382
0.8605	High Similarity	NPC470851
0.8594	High Similarity	NPC42399
0.8594	High Similarity	NPC287423
0.8593	High Similarity	NPC5153
0.8593	High Similarity	NPC48414
0.855	High Similarity	NPC88668
0.8538	High Similarity	NPC471170
0.8527	High Similarity	NPC476859
0.8527	High Similarity	NPC470850
0.8473	Intermediate Similarity	NPC471855
0.8462	Intermediate Similarity	NPC472770
0.8462	Intermediate Similarity	NPC473593
0.845	Intermediate Similarity	NPC298841
0.845	Intermediate Similarity	NPC469757
0.845	Intermediate Similarity	NPC473253
0.845	Intermediate Similarity	NPC473265
0.845	Intermediate Similarity	NPC117702
0.845	Intermediate Similarity	NPC471357
0.845	Intermediate Similarity	NPC146456
0.8438	Intermediate Similarity	NPC470922
0.8413	Intermediate Similarity	NPC472004
0.8397	Intermediate Similarity	NPC476855
0.8397	Intermediate Similarity	NPC476863
0.8397	Intermediate Similarity	NPC213634
0.8397	Intermediate Similarity	NPC473838
0.8397	Intermediate Similarity	NPC475389
0.8397	Intermediate Similarity	NPC476862
0.8394	Intermediate Similarity	NPC471171
0.8387	Intermediate Similarity	NPC138372
0.8387	Intermediate Similarity	NPC106228
0.8382	Intermediate Similarity	NPC25887
0.8359	Intermediate Similarity	NPC27363
0.8346	Intermediate Similarity	NPC46570
0.8346	Intermediate Similarity	NPC478072
0.8333	Intermediate Similarity	NPC472769
0.8333	Intermediate Similarity	NPC231240
0.8333	Intermediate Similarity	NPC475139
0.8333	Intermediate Similarity	NPC180902
0.8321	Intermediate Similarity	NPC469753
0.8321	Intermediate Similarity	NPC471359
0.8321	Intermediate Similarity	NPC219085
0.8321	Intermediate Similarity	NPC251866
0.8321	Intermediate Similarity	NPC471352
0.8321	Intermediate Similarity	NPC9499
0.8321	Intermediate Similarity	NPC86159
0.8321	Intermediate Similarity	NPC284406
0.8321	Intermediate Similarity	NPC469752
0.8321	Intermediate Similarity	NPC17896
0.8321	Intermediate Similarity	NPC471407
0.8321	Intermediate Similarity	NPC197707
0.8321	Intermediate Similarity	NPC471358
0.8321	Intermediate Similarity	NPC180079
0.8321	Intermediate Similarity	NPC471361
0.8321	Intermediate Similarity	NPC469754
0.8321	Intermediate Similarity	NPC70542
0.8321	Intermediate Similarity	NPC476854
0.8321	Intermediate Similarity	NPC469751
0.8321	Intermediate Similarity	NPC89514
0.8321	Intermediate Similarity	NPC6108
0.8321	Intermediate Similarity	NPC10823
0.8321	Intermediate Similarity	NPC469755
0.8321	Intermediate Similarity	NPC471360
0.8308	Intermediate Similarity	NPC470882
0.8308	Intermediate Similarity	NPC305496
0.8306	Intermediate Similarity	NPC178289
0.8295	Intermediate Similarity	NPC8369
0.8284	Intermediate Similarity	NPC171619
0.8281	Intermediate Similarity	NPC470419
0.8281	Intermediate Similarity	NPC107493
0.8271	Intermediate Similarity	NPC58029
0.8271	Intermediate Similarity	NPC316915
0.8271	Intermediate Similarity	NPC469673
0.8258	Intermediate Similarity	NPC220757
0.8258	Intermediate Similarity	NPC173347
0.8258	Intermediate Similarity	NPC196921
0.8254	Intermediate Similarity	NPC474286
0.8254	Intermediate Similarity	NPC475130
0.8244	Intermediate Similarity	NPC476078
0.8244	Intermediate Similarity	NPC245094
0.8244	Intermediate Similarity	NPC476091
0.8231	Intermediate Similarity	NPC250556
0.8231	Intermediate Similarity	NPC222307
0.8231	Intermediate Similarity	NPC469750
0.8217	Intermediate Similarity	NPC469789
0.8217	Intermediate Similarity	NPC120724
0.8217	Intermediate Similarity	NPC472768
0.8209	Intermediate Similarity	NPC100017
0.8209	Intermediate Similarity	NPC475500
0.8209	Intermediate Similarity	NPC182266
0.8209	Intermediate Similarity	NPC475376
0.8209	Intermediate Similarity	NPC223356
0.8209	Intermediate Similarity	NPC471137
0.8209	Intermediate Similarity	NPC473548
0.8209	Intermediate Similarity	NPC471136
0.8209	Intermediate Similarity	NPC475154
0.8209	Intermediate Similarity	NPC476823
0.8203	Intermediate Similarity	NPC472000
0.8203	Intermediate Similarity	NPC472001
0.8203	Intermediate Similarity	NPC471999
0.8203	Intermediate Similarity	NPC470418
0.8195	Intermediate Similarity	NPC34963
0.8189	Intermediate Similarity	NPC477092
0.8188	Intermediate Similarity	NPC470426
0.8182	Intermediate Similarity	NPC35109
0.8182	Intermediate Similarity	NPC231529
0.8182	Intermediate Similarity	NPC162495
0.8175	Intermediate Similarity	NPC476825
0.8168	Intermediate Similarity	NPC471356
0.8168	Intermediate Similarity	NPC179412
0.8168	Intermediate Similarity	NPC329784
0.8168	Intermediate Similarity	NPC152091
0.8168	Intermediate Similarity	NPC240070
0.8154	Intermediate Similarity	NPC473255
0.8148	Intermediate Similarity	NPC219058
0.8148	Intermediate Similarity	NPC256618
0.814	Intermediate Similarity	NPC23786
0.814	Intermediate Similarity	NPC470265
0.8134	Intermediate Similarity	NPC146857
0.8134	Intermediate Similarity	NPC116075
0.8134	Intermediate Similarity	NPC469749
0.8134	Intermediate Similarity	NPC247190
0.8134	Intermediate Similarity	NPC32793
0.8134	Intermediate Similarity	NPC469674
0.8125	Intermediate Similarity	NPC79579
0.8125	Intermediate Similarity	NPC109607
0.8125	Intermediate Similarity	NPC107338
0.8125	Intermediate Similarity	NPC474585
0.812	Intermediate Similarity	NPC251564
0.812	Intermediate Similarity	NPC477189
0.812	Intermediate Similarity	NPC241935
0.812	Intermediate Similarity	NPC279478
0.812	Intermediate Similarity	NPC475606
0.812	Intermediate Similarity	NPC475314
0.811	Intermediate Similarity	NPC475401
0.8106	Intermediate Similarity	NPC270109
0.8106	Intermediate Similarity	NPC473888
0.8092	Intermediate Similarity	NPC174367
0.8092	Intermediate Similarity	NPC93368
0.8092	Intermediate Similarity	NPC47113
0.8092	Intermediate Similarity	NPC217901
0.8092	Intermediate Similarity	NPC293112
0.8088	Intermediate Similarity	NPC68282
0.8077	Intermediate Similarity	NPC469382
0.8077	Intermediate Similarity	NPC204812
0.8077	Intermediate Similarity	NPC129992
0.8074	Intermediate Similarity	NPC329636
0.8062	Intermediate Similarity	NPC67569
0.8062	Intermediate Similarity	NPC204731
0.8062	Intermediate Similarity	NPC470829
0.8062	Intermediate Similarity	NPC473256
0.8062	Intermediate Similarity	NPC202051
0.8062	Intermediate Similarity	NPC470878
0.8062	Intermediate Similarity	NPC473228
0.806	Intermediate Similarity	NPC42670
0.806	Intermediate Similarity	NPC473485
0.806	Intermediate Similarity	NPC474508
0.806	Intermediate Similarity	NPC19124
0.8047	Intermediate Similarity	NPC319570
0.8047	Intermediate Similarity	NPC473203
0.8047	Intermediate Similarity	NPC476529
0.8047	Intermediate Similarity	NPC61520
0.8047	Intermediate Similarity	NPC5292
0.8047	Intermediate Similarity	NPC475775
0.8045	Intermediate Similarity	NPC476966
0.8045	Intermediate Similarity	NPC276838
0.8045	Intermediate Similarity	NPC13071
0.8045	Intermediate Similarity	NPC140092
0.8045	Intermediate Similarity	NPC232785
0.8045	Intermediate Similarity	NPC125077
0.8045	Intermediate Similarity	NPC188234
0.8045	Intermediate Similarity	NPC329986
0.8031	Intermediate Similarity	NPC475305
0.8031	Intermediate Similarity	NPC239273
0.8031	Intermediate Similarity	NPC23046
0.803	Intermediate Similarity	NPC168849
0.803	Intermediate Similarity	NPC475273
0.8015	Intermediate Similarity	NPC194716
0.8015	Intermediate Similarity	NPC32868
0.8015	Intermediate Similarity	NPC86346
0.8015	Intermediate Similarity	NPC473709
0.8015	Intermediate Similarity	NPC75856
0.8015	Intermediate Similarity	NPC473919
0.8015	Intermediate Similarity	NPC241456
0.8015	Intermediate Similarity	NPC469379
0.8015	Intermediate Similarity	NPC172154
0.8015	Intermediate Similarity	NPC81736

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 NPC471234 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	1796
0.2-0.3	3827
0.3-0.4	2163
0.4-0.5	642
0.5-0.6	259
0.6-0.7	147
0.7-0.8	58
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8425	Intermediate Similarity	NPD6370	Approved
0.8385	Intermediate Similarity	NPD7736	Approved
0.8321	Intermediate Similarity	NPD7319	Approved
0.8308	Intermediate Similarity	NPD7078	Approved
0.8295	Intermediate Similarity	NPD7492	Approved
0.8268	Intermediate Similarity	NPD6054	Approved
0.8231	Intermediate Similarity	NPD7507	Approved
0.8231	Intermediate Similarity	NPD6616	Approved
0.8168	Intermediate Similarity	NPD8293	Discontinued
0.8125	Intermediate Similarity	NPD6319	Approved
0.8062	Intermediate Similarity	NPD6015	Approved
0.8062	Intermediate Similarity	NPD6016	Approved
0.8	Intermediate Similarity	NPD5988	Approved
0.7984	Intermediate Similarity	NPD6059	Approved
0.7752	Intermediate Similarity	NPD7115	Discovery
0.7717	Intermediate Similarity	NPD6882	Approved
0.7717	Intermediate Similarity	NPD8297	Approved
0.7692	Intermediate Similarity	NPD7327	Approved
0.7692	Intermediate Similarity	NPD7328	Approved
0.768	Intermediate Similarity	NPD6686	Approved
0.7652	Intermediate Similarity	NPD8033	Approved
0.7634	Intermediate Similarity	NPD7516	Approved
0.7615	Intermediate Similarity	NPD6009	Approved
0.7576	Intermediate Similarity	NPD8377	Approved
0.7576	Intermediate Similarity	NPD8294	Approved
0.754	Intermediate Similarity	NPD6899	Approved
0.754	Intermediate Similarity	NPD6881	Approved
0.7519	Intermediate Similarity	NPD8378	Approved
0.7519	Intermediate Similarity	NPD4632	Approved
0.7519	Intermediate Similarity	NPD8380	Approved
0.7519	Intermediate Similarity	NPD8296	Approved
0.7519	Intermediate Similarity	NPD8335	Approved
0.7519	Intermediate Similarity	NPD8379	Approved
0.7519	Intermediate Similarity	NPD7503	Approved
0.75	Intermediate Similarity	NPD6650	Approved
0.75	Intermediate Similarity	NPD6649	Approved
0.746	Intermediate Similarity	NPD5697	Approved
0.7445	Intermediate Similarity	NPD6033	Approved
0.7422	Intermediate Similarity	NPD4634	Approved
0.7422	Intermediate Similarity	NPD6883	Approved
0.7422	Intermediate Similarity	NPD7290	Approved
0.7422	Intermediate Similarity	NPD7102	Approved
0.7407	Intermediate Similarity	NPD8328	Phase 3
0.7407	Intermediate Similarity	NPD7604	Phase 2
0.7402	Intermediate Similarity	NPD7320	Approved
0.7381	Intermediate Similarity	NPD7128	Approved
0.7381	Intermediate Similarity	NPD5739	Approved
0.7381	Intermediate Similarity	NPD6402	Approved
0.7381	Intermediate Similarity	NPD6675	Approved
0.7364	Intermediate Similarity	NPD6617	Approved
0.7364	Intermediate Similarity	NPD8130	Phase 1
0.7364	Intermediate Similarity	NPD6869	Approved
0.7364	Intermediate Similarity	NPD6847	Approved
0.7344	Intermediate Similarity	NPD6373	Approved
0.7344	Intermediate Similarity	NPD6372	Approved
0.7344	Intermediate Similarity	NPD6014	Approved
0.7344	Intermediate Similarity	NPD6012	Approved
0.7344	Intermediate Similarity	NPD6013	Approved
0.7323	Intermediate Similarity	NPD6412	Phase 2
0.7323	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD6371	Approved
0.7266	Intermediate Similarity	NPD6011	Approved
0.7259	Intermediate Similarity	NPD5983	Phase 2
0.7259	Intermediate Similarity	NPD8517	Approved
0.7259	Intermediate Similarity	NPD8515	Approved
0.7259	Intermediate Similarity	NPD8513	Phase 3
0.7259	Intermediate Similarity	NPD8516	Approved
0.7244	Intermediate Similarity	NPD6008	Approved
0.7188	Intermediate Similarity	NPD5701	Approved
0.7174	Intermediate Similarity	NPD6336	Discontinued
0.7143	Intermediate Similarity	NPD5211	Phase 2
0.7132	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5956	Approved
0.709	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6053	Discontinued
0.704	Intermediate Similarity	NPD4225	Approved
0.7031	Intermediate Similarity	NPD5141	Approved
0.7012	Intermediate Similarity	NPD7799	Discontinued
0.6992	Remote Similarity	NPD8133	Approved
0.6985	Remote Similarity	NPD7101	Approved
0.6985	Remote Similarity	NPD7100	Approved
0.6984	Remote Similarity	NPD4696	Approved
0.6984	Remote Similarity	NPD7640	Approved
0.6984	Remote Similarity	NPD5285	Approved
0.6984	Remote Similarity	NPD7639	Approved
0.6984	Remote Similarity	NPD5286	Approved
0.697	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.696	Remote Similarity	NPD6084	Phase 2
0.696	Remote Similarity	NPD6083	Phase 2
0.6947	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6335	Approved
0.6905	Remote Similarity	NPD7638	Approved
0.6889	Remote Similarity	NPD6274	Approved
0.6885	Remote Similarity	NPD6698	Approved
0.6885	Remote Similarity	NPD46	Approved
0.6875	Remote Similarity	NPD4633	Approved
0.6875	Remote Similarity	NPD5225	Approved
0.6875	Remote Similarity	NPD5224	Approved
0.6875	Remote Similarity	NPD5226	Approved
0.6842	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6317	Approved
0.6825	Remote Similarity	NPD4755	Approved
0.6822	Remote Similarity	NPD5175	Approved
0.6822	Remote Similarity	NPD5174	Approved
0.6806	Remote Similarity	NPD7260	Phase 2
0.68	Remote Similarity	NPD5695	Phase 3
0.6797	Remote Similarity	NPD5344	Discontinued
0.6797	Remote Similarity	NPD5223	Approved
0.6788	Remote Similarity	NPD6314	Approved
0.6788	Remote Similarity	NPD6313	Approved
0.6786	Remote Similarity	NPD6067	Discontinued
0.6767	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD8074	Phase 3
0.6748	Remote Similarity	NPD5785	Approved
0.6742	Remote Similarity	NPD4730	Approved
0.6742	Remote Similarity	NPD4729	Approved
0.6719	Remote Similarity	NPD4700	Approved
0.6689	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7642	Approved
0.6667	Remote Similarity	NPD1700	Approved
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7830	Approved
0.6667	Remote Similarity	NPD7829	Approved
0.6644	Remote Similarity	NPD6845	Suspended
0.6644	Remote Similarity	NPD6333	Approved
0.6644	Remote Similarity	NPD6334	Approved
0.6643	Remote Similarity	NPD6921	Approved
0.6643	Remote Similarity	NPD6909	Approved
0.6643	Remote Similarity	NPD6908	Approved
0.6642	Remote Similarity	NPD5250	Approved
0.6642	Remote Similarity	NPD5248	Approved
0.6642	Remote Similarity	NPD5247	Approved
0.6642	Remote Similarity	NPD5249	Phase 3
0.6642	Remote Similarity	NPD5251	Approved
0.6641	Remote Similarity	NPD5696	Approved
0.6591	Remote Similarity	NPD4767	Approved
0.6591	Remote Similarity	NPD4768	Approved
0.6587	Remote Similarity	NPD5282	Discontinued
0.6567	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.656	Remote Similarity	NPD5693	Phase 1
0.656	Remote Similarity	NPD7983	Approved
0.6541	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6868	Approved
0.6515	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD5779	Approved
0.6508	Remote Similarity	NPD5778	Approved
0.65	Remote Similarity	NPD4522	Approved
0.6493	Remote Similarity	NPD5128	Approved
0.6489	Remote Similarity	NPD7632	Discontinued
0.6484	Remote Similarity	NPD5222	Approved
0.6484	Remote Similarity	NPD5221	Approved
0.6484	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7838	Discovery
0.6479	Remote Similarity	NPD8080	Discontinued
0.6471	Remote Similarity	NPD5215	Approved
0.6471	Remote Similarity	NPD5217	Approved
0.6471	Remote Similarity	NPD5216	Approved
0.6462	Remote Similarity	NPD6648	Approved
0.6439	Remote Similarity	NPD4754	Approved
0.6434	Remote Similarity	NPD5173	Approved
0.6429	Remote Similarity	NPD6079	Approved
0.6429	Remote Similarity	NPD7637	Suspended
0.641	Remote Similarity	NPD7625	Phase 1
0.6406	Remote Similarity	NPD4629	Approved
0.6406	Remote Similarity	NPD5210	Approved
0.64	Remote Similarity	NPD6080	Approved
0.64	Remote Similarity	NPD4753	Phase 2
0.64	Remote Similarity	NPD6673	Approved
0.64	Remote Similarity	NPD6904	Approved
0.6397	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD5169	Approved
0.6397	Remote Similarity	NPD5135	Approved
0.637	Remote Similarity	NPD8337	Approved
0.637	Remote Similarity	NPD8336	Approved
0.635	Remote Similarity	NPD5127	Approved
0.6341	Remote Similarity	NPD5363	Approved
0.6329	Remote Similarity	NPD7236	Approved
0.632	Remote Similarity	NPD6672	Approved
0.632	Remote Similarity	NPD5737	Approved
0.6309	Remote Similarity	NPD8338	Approved
0.6299	Remote Similarity	NPD6411	Approved
0.6299	Remote Similarity	NPD5694	Approved
0.6299	Remote Similarity	NPD6050	Approved
0.6294	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.629	Remote Similarity	NPD5786	Approved
0.627	Remote Similarity	NPD5328	Approved
0.627	Remote Similarity	NPD1695	Approved
0.625	Remote Similarity	NPD6399	Phase 3
0.625	Remote Similarity	NPD4202	Approved
0.624	Remote Similarity	NPD4250	Approved
0.624	Remote Similarity	NPD4251	Approved
0.6235	Remote Similarity	NPD7239	Suspended
0.6233	Remote Similarity	NPD8451	Approved
0.6231	Remote Similarity	NPD4697	Phase 3
0.6231	Remote Similarity	NPD7839	Suspended

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