NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	336.23
Volume:	352.775
LogP:	2.581
LogD:	2.723
LogS:	-3.44
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.686
Synthetic Accessibility Score:	5.91
Fsp3:	0.95
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.782
MDCK Permeability:	1.6446916561108083e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.215
30% Bioavailability (F30%):	0.857

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.633
Plasma Protein Binding (PPB):	77.01152038574219%
Volume Distribution (VD):	1.005
Pgp-substrate:	29.391029357910156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.475
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.766
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.226
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.261
CYP3A4-inhibitor:	0.546
CYP3A4-substrate:	0.144

ADMET: Excretion

Clearance (CL):	6.369
Half-life (T1/2):	0.73

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.272
Drug-inuced Liver Injury (DILI):	0.099
AMES Toxicity:	0.258
Rat Oral Acute Toxicity:	0.382
Maximum Recommended Daily Dose:	0.19
Skin Sensitization:	0.135
Carcinogencity:	0.124
Eye Corrosion:	0.195
Eye Irritation:	0.127
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: NPC476727

Natural Product ID:	NPC476727
*Common Name:**	7beta,16alpha,17-Trihydroxy-ent-kauran-6-one
IUPAC Name:	(1R,2R,4R,9S,10S,13S,14R)-2,14-dihydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecan-3-one
Synonyms:	Broussonetone B
Standard InCHIKey:	DXKOYDRYFOHLGA-DOJQOKQASA-N
Standard InCHI:	InChI=1S/C20H32O4/c1-17(2)7-4-8-18(3)13-6-5-12-9-19(13,10-20(12,24)11-21)16(23)14(22)15(17)18/h12-13,15-16,21,23-24H,4-11H2,1-3H3/t12-,13-,15+,16-,18-,19+,20-/m0/s1
SMILES:	C[C@@]12CCCC([C@H]1C(=O)[C@@H]([C@]34[C@H]2CC[C@@H](C3)[C@](C4)(CO)O)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	25157279
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane 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
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[11395279]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	n.a.	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	Shawnee National Forest, Harrisburg, IL, US	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12419367]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	leaves	Kaohsiung, Taiwan	2006-SEP	PMID[18986201]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[19296617]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358644]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5495	Broussonetia papyrifera	Species	Moraceae	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	3

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	317000	nM	PMID[18986201]
NPT2	Others	Unspecified		IC50	=	69650	nM	PMID[18986201]
NPT2	Others	Unspecified		IC50	=	53900	nM	PMID[18986201]

☑ 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 NPC476727 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	387
0.1-0.2	3371
0.2-0.3	9900
0.3-0.4	13585
0.4-0.5	5831
0.5-0.6	5150
0.6-0.7	3390
0.7-0.8	920
0.8-0.85	128
0.85-0.9	20
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476726
0.9383	High Similarity	NPC327451
0.9277	High Similarity	NPC472272
0.9024	High Similarity	NPC317066
0.9012	High Similarity	NPC470609
0.8941	High Similarity	NPC263802
0.8902	High Similarity	NPC469745
0.8824	High Similarity	NPC80700
0.881	High Similarity	NPC50438
0.8778	High Similarity	NPC476728
0.8636	High Similarity	NPC476296
0.8625	High Similarity	NPC159789
0.8571	High Similarity	NPC121121
0.8571	High Similarity	NPC328007
0.8571	High Similarity	NPC268040
0.8519	High Similarity	NPC472486
0.8519	High Similarity	NPC472487
0.8506	High Similarity	NPC202937
0.85	High Similarity	NPC472854
0.85	High Similarity	NPC254340
0.8462	Intermediate Similarity	NPC305808
0.8434	Intermediate Similarity	NPC320144
0.8415	Intermediate Similarity	NPC475031
0.8415	Intermediate Similarity	NPC221420
0.8395	Intermediate Similarity	NPC125767
0.8395	Intermediate Similarity	NPC21220
0.8395	Intermediate Similarity	NPC317242
0.8375	Intermediate Similarity	NPC232112
0.8375	Intermediate Similarity	NPC470610
0.8375	Intermediate Similarity	NPC153719
0.8352	Intermediate Similarity	NPC470424
0.8333	Intermediate Similarity	NPC52756
0.8315	Intermediate Similarity	NPC56962
0.8315	Intermediate Similarity	NPC24705
0.8313	Intermediate Similarity	NPC224802
0.8313	Intermediate Similarity	NPC80089
0.8313	Intermediate Similarity	NPC34046
0.8313	Intermediate Similarity	NPC171426
0.8313	Intermediate Similarity	NPC185465
0.8313	Intermediate Similarity	NPC324700
0.8313	Intermediate Similarity	NPC478084
0.8293	Intermediate Similarity	NPC475742
0.8293	Intermediate Similarity	NPC163597
0.8293	Intermediate Similarity	NPC5767
0.8272	Intermediate Similarity	NPC48795
0.8261	Intermediate Similarity	NPC470031
0.825	Intermediate Similarity	NPC320549
0.825	Intermediate Similarity	NPC151018
0.825	Intermediate Similarity	NPC156277
0.825	Intermediate Similarity	NPC58057
0.8242	Intermediate Similarity	NPC476189
0.8235	Intermediate Similarity	NPC12933
0.8222	Intermediate Similarity	NPC475056
0.8222	Intermediate Similarity	NPC77756
0.8214	Intermediate Similarity	NPC201276
0.8214	Intermediate Similarity	NPC80891
0.8193	Intermediate Similarity	NPC477227
0.8193	Intermediate Similarity	NPC192046
0.8193	Intermediate Similarity	NPC128951
0.8193	Intermediate Similarity	NPC180199
0.8193	Intermediate Similarity	NPC23884
0.8193	Intermediate Similarity	NPC302578
0.8193	Intermediate Similarity	NPC477919
0.8193	Intermediate Similarity	NPC264602
0.8193	Intermediate Similarity	NPC207010
0.8193	Intermediate Similarity	NPC105208
0.8193	Intermediate Similarity	NPC317913
0.8193	Intermediate Similarity	NPC185915
0.8191	Intermediate Similarity	NPC476294
0.8182	Intermediate Similarity	NPC474448
0.8171	Intermediate Similarity	NPC24014
0.8171	Intermediate Similarity	NPC97534
0.8171	Intermediate Similarity	NPC195155
0.8171	Intermediate Similarity	NPC27349
0.8171	Intermediate Similarity	NPC174964
0.8171	Intermediate Similarity	NPC273366
0.8152	Intermediate Similarity	NPC470423
0.8148	Intermediate Similarity	NPC310766
0.8125	Intermediate Similarity	NPC232925
0.8125	Intermediate Similarity	NPC251201
0.8125	Intermediate Similarity	NPC63588
0.8118	Intermediate Similarity	NPC477851
0.8111	Intermediate Similarity	NPC61688
0.8105	Intermediate Similarity	NPC15390
0.8095	Intermediate Similarity	NPC18857
0.8095	Intermediate Similarity	NPC67657
0.8095	Intermediate Similarity	NPC199965
0.8095	Intermediate Similarity	NPC476732
0.8085	Intermediate Similarity	NPC170978
0.8072	Intermediate Similarity	NPC4209
0.8065	Intermediate Similarity	NPC287354
0.8065	Intermediate Similarity	NPC62407
0.8049	Intermediate Similarity	NPC304499
0.8049	Intermediate Similarity	NPC133922
0.8046	Intermediate Similarity	NPC268578
0.8046	Intermediate Similarity	NPC217559
0.8046	Intermediate Similarity	NPC292458
0.8043	Intermediate Similarity	NPC161035
0.8041	Intermediate Similarity	NPC191892
0.8025	Intermediate Similarity	NPC89310
0.8023	Intermediate Similarity	NPC254123
0.8022	Intermediate Similarity	NPC100313
0.8022	Intermediate Similarity	NPC46758
0.8	Intermediate Similarity	NPC31302
0.8	Intermediate Similarity	NPC213178
0.8	Intermediate Similarity	NPC321732
0.8	Intermediate Similarity	NPC477614
0.8	Intermediate Similarity	NPC287452
0.8	Intermediate Similarity	NPC327728
0.8	Intermediate Similarity	NPC226491
0.8	Intermediate Similarity	NPC6120
0.8	Intermediate Similarity	NPC66407
0.8	Intermediate Similarity	NPC477820
0.8	Intermediate Similarity	NPC245029
0.8	Intermediate Similarity	NPC324607
0.8	Intermediate Similarity	NPC131892
0.7979	Intermediate Similarity	NPC116683
0.7978	Intermediate Similarity	NPC472745
0.7978	Intermediate Similarity	NPC302111
0.7959	Intermediate Similarity	NPC327093
0.7957	Intermediate Similarity	NPC76136
0.7957	Intermediate Similarity	NPC329713
0.7957	Intermediate Similarity	NPC217567
0.7955	Intermediate Similarity	NPC474996
0.7955	Intermediate Similarity	NPC471044
0.7955	Intermediate Similarity	NPC473336
0.7952	Intermediate Similarity	NPC196136
0.7952	Intermediate Similarity	NPC212733
0.7952	Intermediate Similarity	NPC243027
0.7952	Intermediate Similarity	NPC158208
0.7931	Intermediate Similarity	NPC61107
0.7931	Intermediate Similarity	NPC30583
0.7931	Intermediate Similarity	NPC289486
0.7927	Intermediate Similarity	NPC81759
0.7907	Intermediate Similarity	NPC472853
0.7895	Intermediate Similarity	NPC190554
0.7895	Intermediate Similarity	NPC471241
0.7889	Intermediate Similarity	NPC470920
0.7889	Intermediate Similarity	NPC239938
0.7882	Intermediate Similarity	NPC471045
0.7872	Intermediate Similarity	NPC17336
0.7865	Intermediate Similarity	NPC266651
0.7857	Intermediate Similarity	NPC117185
0.7849	Intermediate Similarity	NPC472496
0.7843	Intermediate Similarity	NPC473062
0.7841	Intermediate Similarity	NPC269684
0.7841	Intermediate Similarity	NPC472744
0.7835	Intermediate Similarity	NPC477172
0.7835	Intermediate Similarity	NPC178853
0.7831	Intermediate Similarity	NPC280026
0.7831	Intermediate Similarity	NPC192501
0.7831	Intermediate Similarity	NPC10476
0.7831	Intermediate Similarity	NPC167702
0.7831	Intermediate Similarity	NPC228994
0.7826	Intermediate Similarity	NPC136801
0.7822	Intermediate Similarity	NPC227879
0.7822	Intermediate Similarity	NPC208333
0.7816	Intermediate Similarity	NPC476071
0.7816	Intermediate Similarity	NPC77311
0.7805	Intermediate Similarity	NPC127094
0.7805	Intermediate Similarity	NPC187471
0.7805	Intermediate Similarity	NPC252182
0.7805	Intermediate Similarity	NPC1340
0.7805	Intermediate Similarity	NPC470071
0.7802	Intermediate Similarity	NPC90676
0.78	Intermediate Similarity	NPC165873
0.7791	Intermediate Similarity	NPC476176
0.7791	Intermediate Similarity	NPC472310
0.7789	Intermediate Similarity	NPC49371
0.7778	Intermediate Similarity	NPC248216
0.7778	Intermediate Similarity	NPC107919
0.7778	Intermediate Similarity	NPC92139
0.7778	Intermediate Similarity	NPC100078
0.7778	Intermediate Similarity	NPC29705
0.7766	Intermediate Similarity	NPC280804
0.7766	Intermediate Similarity	NPC206878
0.7766	Intermediate Similarity	NPC477495
0.7765	Intermediate Similarity	NPC64081
0.7765	Intermediate Similarity	NPC298168
0.7765	Intermediate Similarity	NPC143133
0.7765	Intermediate Similarity	NPC474574
0.7755	Intermediate Similarity	NPC244969
0.7755	Intermediate Similarity	NPC470172
0.7755	Intermediate Similarity	NPC213528
0.7753	Intermediate Similarity	NPC105895
0.775	Intermediate Similarity	NPC63190
0.775	Intermediate Similarity	NPC472984
0.7738	Intermediate Similarity	NPC267753
0.7732	Intermediate Similarity	NPC41843
0.7727	Intermediate Similarity	NPC477935
0.7727	Intermediate Similarity	NPC202688
0.7727	Intermediate Similarity	NPC475388
0.7727	Intermediate Similarity	NPC154043
0.7727	Intermediate Similarity	NPC60018
0.7723	Intermediate Similarity	NPC316930
0.7717	Intermediate Similarity	NPC477443
0.7717	Intermediate Similarity	NPC477440
0.7708	Intermediate Similarity	NPC472273
0.7708	Intermediate Similarity	NPC18509
0.77	Intermediate Similarity	NPC214264

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 NPC476727 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	418
0.1-0.2	3718
0.2-0.3	3397
0.3-0.4	976
0.4-0.5	267
0.5-0.6	174
0.6-0.7	120
0.7-0.8	65
0.8-0.85	14
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8625	High Similarity	NPD3703	Phase 2
0.8313	Intermediate Similarity	NPD6118	Approved
0.8313	Intermediate Similarity	NPD6697	Approved
0.8313	Intermediate Similarity	NPD6114	Approved
0.8313	Intermediate Similarity	NPD6115	Approved
0.825	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6116	Phase 1
0.8125	Intermediate Similarity	NPD4244	Approved
0.8125	Intermediate Similarity	NPD4789	Approved
0.8125	Intermediate Similarity	NPD4245	Approved
0.8072	Intermediate Similarity	NPD6117	Approved
0.8	Intermediate Similarity	NPD3698	Phase 2
0.8	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD5360	Phase 3
0.7875	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD4755	Approved
0.76	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD4634	Approved
0.7551	Intermediate Similarity	NPD4700	Approved
0.7551	Intermediate Similarity	NPD5286	Approved
0.7551	Intermediate Similarity	NPD5285	Approved
0.7551	Intermediate Similarity	NPD4696	Approved
0.75	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD5223	Approved
0.74	Intermediate Similarity	NPD5225	Approved
0.74	Intermediate Similarity	NPD4633	Approved
0.74	Intermediate Similarity	NPD5226	Approved
0.74	Intermediate Similarity	NPD5224	Approved
0.74	Intermediate Similarity	NPD5211	Phase 2
0.7381	Intermediate Similarity	NPD4758	Discontinued
0.7358	Intermediate Similarity	NPD4632	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
0.7327	Intermediate Similarity	NPD5174	Approved
0.7327	Intermediate Similarity	NPD5175	Approved
0.7327	Intermediate Similarity	NPD4754	Approved
0.7326	Intermediate Similarity	NPD3702	Approved
0.7273	Intermediate Similarity	NPD5364	Discontinued
0.7273	Intermediate Similarity	NPD3671	Phase 1
0.7262	Intermediate Similarity	NPD4787	Phase 1
0.7255	Intermediate Similarity	NPD5141	Approved
0.7253	Intermediate Similarity	NPD4788	Approved
0.7212	Intermediate Similarity	NPD6881	Approved
0.7212	Intermediate Similarity	NPD7320	Approved
0.7212	Intermediate Similarity	NPD6899	Approved
0.7184	Intermediate Similarity	NPD4768	Approved
0.7184	Intermediate Similarity	NPD4767	Approved
0.7176	Intermediate Similarity	NPD5777	Approved
0.7176	Intermediate Similarity	NPD6081	Approved
0.7158	Intermediate Similarity	NPD5328	Approved
0.7143	Intermediate Similarity	NPD6373	Approved
0.7143	Intermediate Similarity	NPD6372	Approved
0.7115	Intermediate Similarity	NPD5701	Approved
0.7115	Intermediate Similarity	NPD5697	Approved
0.7113	Intermediate Similarity	NPD4202	Approved
0.7103	Intermediate Similarity	NPD8297	Approved
0.7097	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7290	Approved
0.7075	Intermediate Similarity	NPD7102	Approved
0.7075	Intermediate Similarity	NPD6883	Approved
0.7071	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5221	Approved
0.7071	Intermediate Similarity	NPD4697	Phase 3
0.7071	Intermediate Similarity	NPD5222	Approved
0.7048	Intermediate Similarity	NPD4730	Approved
0.7048	Intermediate Similarity	NPD6011	Approved
0.7048	Intermediate Similarity	NPD4729	Approved
0.7048	Intermediate Similarity	NPD5128	Approved
0.701	Intermediate Similarity	NPD6079	Approved
0.7009	Intermediate Similarity	NPD6650	Approved
0.7009	Intermediate Similarity	NPD8130	Phase 1
0.7009	Intermediate Similarity	NPD6847	Approved
0.7009	Intermediate Similarity	NPD6617	Approved
0.7009	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6649	Approved
0.7009	Intermediate Similarity	NPD6869	Approved
0.7	Intermediate Similarity	NPD6009	Approved
0.7	Intermediate Similarity	NPD5173	Approved
0.6988	Remote Similarity	NPD4224	Phase 2
0.6981	Remote Similarity	NPD6012	Approved
0.6981	Remote Similarity	NPD6013	Approved
0.6981	Remote Similarity	NPD6014	Approved
0.6979	Remote Similarity	NPD4753	Phase 2
0.6964	Remote Similarity	NPD6059	Approved
0.6964	Remote Similarity	NPD6054	Approved
0.6964	Remote Similarity	NPD6319	Approved
0.6961	Remote Similarity	NPD1700	Approved
0.6944	Remote Similarity	NPD6882	Approved
0.6923	Remote Similarity	NPD6928	Phase 2
0.6916	Remote Similarity	NPD5249	Phase 3
0.6916	Remote Similarity	NPD5169	Approved
0.6916	Remote Similarity	NPD5251	Approved
0.6916	Remote Similarity	NPD5250	Approved
0.6916	Remote Similarity	NPD5135	Approved
0.6916	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5247	Approved
0.6916	Remote Similarity	NPD5248	Approved
0.6887	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5127	Approved
0.6852	Remote Similarity	NPD5215	Approved
0.6852	Remote Similarity	NPD5216	Approved
0.6852	Remote Similarity	NPD5217	Approved
0.6842	Remote Similarity	NPD6370	Approved
0.6837	Remote Similarity	NPD8034	Phase 2
0.6837	Remote Similarity	NPD8035	Phase 2
0.6809	Remote Similarity	NPD4786	Approved
0.6783	Remote Similarity	NPD7604	Phase 2
0.6754	Remote Similarity	NPD6015	Approved
0.6754	Remote Similarity	NPD5983	Phase 2
0.6754	Remote Similarity	NPD6016	Approved
0.6739	Remote Similarity	NPD7525	Registered
0.6737	Remote Similarity	NPD5329	Approved
0.6724	Remote Similarity	NPD7492	Approved
0.6699	Remote Similarity	NPD8418	Phase 2
0.6696	Remote Similarity	NPD5988	Approved
0.6695	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD5167	Approved
0.6637	Remote Similarity	NPD6335	Approved
0.6634	Remote Similarity	NPD4629	Approved
0.6634	Remote Similarity	NPD5210	Approved
0.6632	Remote Similarity	NPD4197	Approved
0.6632	Remote Similarity	NPD3665	Phase 1
0.6632	Remote Similarity	NPD3666	Approved
0.6632	Remote Similarity	NPD3133	Approved
0.661	Remote Similarity	NPD7078	Approved
0.661	Remote Similarity	NPD8293	Discontinued
0.6607	Remote Similarity	NPD6274	Approved
0.66	Remote Similarity	NPD8171	Discontinued
0.6596	Remote Similarity	NPD3667	Approved
0.6579	Remote Similarity	NPD7100	Approved
0.6579	Remote Similarity	NPD7101	Approved
0.6555	Remote Similarity	NPD6033	Approved
0.6549	Remote Similarity	NPD6317	Approved
0.6542	Remote Similarity	NPD6008	Approved
0.6525	Remote Similarity	NPD7507	Approved
0.6491	Remote Similarity	NPD6314	Approved
0.6491	Remote Similarity	NPD6313	Approved
0.6481	Remote Similarity	NPD6412	Phase 2
0.6466	Remote Similarity	NPD6908	Approved
0.6466	Remote Similarity	NPD6909	Approved
0.6442	Remote Similarity	NPD7638	Approved
0.6436	Remote Similarity	NPD6399	Phase 3
0.6429	Remote Similarity	NPD8133	Approved
0.6422	Remote Similarity	NPD5168	Approved
0.6421	Remote Similarity	NPD4223	Phase 3
0.6421	Remote Similarity	NPD4221	Approved
0.6381	Remote Similarity	NPD7639	Approved
0.6381	Remote Similarity	NPD7640	Approved
0.6364	Remote Similarity	NPD7319	Approved
0.6344	Remote Similarity	NPD3617	Approved
0.6337	Remote Similarity	NPD7515	Phase 2
0.6327	Remote Similarity	NPD5690	Phase 2
0.6327	Remote Similarity	NPD4694	Approved
0.6327	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5280	Approved
0.6327	Remote Similarity	NPD5279	Phase 3
0.6325	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4139	Approved
0.6316	Remote Similarity	NPD4692	Approved
0.6311	Remote Similarity	NPD5695	Phase 3
0.6293	Remote Similarity	NPD4522	Approved
0.6286	Remote Similarity	NPD5696	Approved
0.6265	Remote Similarity	NPD3198	Approved
0.6262	Remote Similarity	NPD7632	Discontinued
0.6261	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6920	Discontinued
0.6186	Remote Similarity	NPD6921	Approved
0.6174	Remote Similarity	NPD6940	Discontinued
0.6174	Remote Similarity	NPD6868	Approved
0.6162	Remote Similarity	NPD4688	Approved
0.6162	Remote Similarity	NPD5205	Approved
0.6162	Remote Similarity	NPD4690	Approved
0.6162	Remote Similarity	NPD4693	Phase 3
0.6162	Remote Similarity	NPD4138	Approved
0.6162	Remote Similarity	NPD4689	Approved
0.6162	Remote Similarity	NPD6098	Approved
0.6139	Remote Similarity	NPD6904	Approved
0.6139	Remote Similarity	NPD6673	Approved
0.6139	Remote Similarity	NPD6080	Approved
0.6122	Remote Similarity	NPD3668	Phase 3
0.6083	Remote Similarity	NPD8328	Phase 3
0.6078	Remote Similarity	NPD6700	Approved
0.6078	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD7748	Approved
0.6042	Remote Similarity	NPD4748	Discontinued
0.604	Remote Similarity	NPD6672	Approved
0.604	Remote Similarity	NPD5737	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