NPASS Compound

Natural Product: NPC242631

Natural Product ID	NPC242631
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OJUYFGQEMPENCE-DPKHZRJYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	120678
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 81 85 0 0 0 0 0 0 0 0999 V2000 -5.4536 2.2383 1.0065 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7953 1.7466 -0.2908 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5718 0.5819 -0.8301 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8037 -0.6505 -1.1027 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4929 -0.3453 -1.7783 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7074 -1.5773 -2.0121 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6233 -2.0059 -1.1285 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9787 -0.8951 -0.2493 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3517 0.3188 -0.9849 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4711 1.0015 -1.6576 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9669 0.6184 -1.7440 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3080 -0.0016 -0.4349 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8062 -0.1276 -0.2110 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5128 -1.1014 -1.0582 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3665 1.2561 -0.6234 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7692 1.4620 -0.0904 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9607 1.1361 1.3372 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3815 -0.1740 1.7691 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2534 -1.3509 1.5064 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2405 -0.0708 3.2971 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9816 -0.2832 1.2562 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2281 -1.4785 1.7825 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7745 -1.2431 1.5095 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4710 -1.1426 -0.0088 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8240 -2.4877 -0.5423 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3033 1.2494 1.6452 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7468 0.7631 -1.0533 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4391 1.1656 0.1809 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7603 2.3660 0.8273 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6729 -1.0616 1.0599 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5157 -2.0072 1.2513 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5158 -0.2698 2.1807 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8678 0.1407 -3.1643 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5300 -0.4603 -4.2082 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6091 1.2886 -3.3150 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0738 3.2454 1.2502 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1524 1.5735 1.8599 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5445 2.2374 0.9253 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6784 2.5960 -0.9510 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1848 0.8366 -1.7404 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3776 0.2934 -0.0828 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3940 -1.2541 -1.8514 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6927 -1.3292 -0.2362 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4783 -2.4201 -2.0200 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3774 -1.6188 -3.1067 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9557 -2.8591 -0.4661 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8693 -2.4720 -1.7966 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7513 1.9282 -2.2189 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5513 1.5304 -1.8960 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1720 -0.0302 -2.6176 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0452 0.8227 0.3150 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9814 -1.2058 -2.0292 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8038 -2.0575 -0.5919 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5094 -0.6588 -1.3696 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7123 2.0721 -0.3264 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5238 1.2195 -1.7370 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9595 2.5692 -0.2140 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5423 0.9781 -0.7286 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4366 1.9322 1.9438 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7198 -2.2931 1.6118 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8233 -1.2814 0.5383 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0696 -1.3696 2.2891 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1933 -1.0579 3.7673 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3824 0.5899 3.5605 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1439 0.4453 3.6926 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4376 0.6049 1.7147 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3107 -1.3643 2.9183 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6470 -2.4426 1.5850 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1934 -1.9888 2.0152 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6485 -0.1776 1.8960 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0188 -3.2093 -0.2104 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7072 -2.9759 -0.0249 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0692 -2.5612 -1.5964 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8584 1.0566 0.8352 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8424 1.6808 -1.7188 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7657 0.3981 0.8748 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6617 2.1879 0.7318 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0022 2.3028 1.9138 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0863 3.3210 0.3919 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1428 -0.2187 2.9474 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6702 1.8258 -4.1685 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 18 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 17 26 1 0 9 27 1 0 27 28 1 0 28 29 1 0 8 30 1 1 30 31 2 0 30 32 1 0 5 33 1 6 33 34 2 0 33 35 1 0 28 2 1 0 27 5 1 0 24 8 1 0 24 12 1 0 21 13 1 0 1 36 1 0 1 37 1 0 1 38 1 0 2 39 1 6 3 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 6 44 1 0 6 45 1 0 7 46 1 0 7 47 1 0 10 48 1 0 11 49 1 0 11 50 1 0 12 51 1 1 14 52 1 0 14 53 1 0 14 54 1 0 15 55 1 0 15 56 1 0 16 57 1 0 16 58 1 0 17 59 1 1 19 60 1 0 19 61 1 0 19 62 1 0 20 63 1 0 20 64 1 0 20 65 1 0 21 66 1 1 22 67 1 0 22 68 1 0 23 69 1 0 23 70 1 0 25 71 1 0 25 72 1 0 25 73 1 0 26 74 1 0 27 75 1 6 28 76 1 1 29 77 1 0 29 78 1 0 29 79 1 0 32 80 1 0 35 81 1 0 M END

Standard InCHIKey	OJUYFGQEMPENCE-DPKHZRJYSA-N
Standard InCHI	InChI=1S/C30H46O5/c1-17-9-14-29(24(32)33)15-16-30(25(34)35)19(23(29)18(17)2)7-8-21-27(5)12-11-22(31)26(3,4)20(27)10-13-28(21,30)6/h7,17-18,20-23,31H,8-16H2,1-6H3,(H,32,33)(H,34,35)/t17-,18+,20+,21-,22+,23+,27+,28-,29+,30-/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]2[C@H]1C)C(=O)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	486.33	Volume:	520.695 ? Van der Waals volume.
Dense:	0.934	LogP:	2.949 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.572 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.781 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	94.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.407	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.87	Fsp³:	0.867
MCE-18:	105.857 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.584	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.017 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.322	Promiscuous compounds:	0.121

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.527	MDCK Permeability:	-5.095
Pgp-inhibitor:	0.0	Pgp-substrate:	0.043
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.599	30% Bioavailability (F30%):	0.076
50% Bioavailability (F50%):	0.868

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114	MRP1:	0.994
Plasma Protein Binding (PPB):	92.769%	Volume Distribution (VD):	-0.643
Fu:	8.242% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.807	BCRP inhibitor:	0.003
BSEP inhibitor:	0.144

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.004	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.221	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

1.479

Half-life (T1/2):

1.385

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.01
Human Hepatotoxicity (H-HT):	0.757	Drug-induced Liver Injury (DILI):	0.846
AMES Toxicity:	0.243	Rat Oral Acute Toxicity:	0.369
Maximum Recommended Daily Dose:	0.283	Skin Sensitization:	0.958
Carcinogencity:	0.923	Eye Corrosion:	0.019
Eye Irritation:	0.795	Respiratory Toxicity:	0.952
Drug-induced Neurotoxicity:	0.014	Ototoxicity:	0.676
Hematotoxicity:	0.484	Drug-induced Nephrotoxicity:	0.928
Genotoxicity:	0.892	RPMI-8226 Immunitoxicity:	0.014
A549 Cytotoxicity:	0.041	Hek293 Cytotoxicity:	0.045
BCF:	0.466 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.278 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.641 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.044 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO25089	Cinchona calisaya	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11992775]
NPO13017	Nauclea latifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31429278]
NPO28120	Anisopappus pinnatifidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18817	Platycarpha glomerata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27221	Prosopis spicigera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4940	Peyrousea umbellata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25089	Cinchona calisaya	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27397	Drymaria cordata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25089	Cinchona calisaya	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27397	Drymaria cordata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19583	Ficus nervosa	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13017	Nauclea latifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28344	Rubus xanthocarpus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18817	Platycarpha glomerata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4940	Peyrousea umbellata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27397	Drymaria cordata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27913	Ageratina tomentella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9061	Euthamia graminifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27722	Caralluma stalagmifera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27221	Prosopis spicigera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28120	Anisopappus pinnatifidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25089	Cinchona calisaya	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28001	Zeora sordida	n.a.	n.a.	n.a.	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	Organism Name	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
MIC	1
MBC	1
Ratio	1

Activity Type	# Activity
Organism	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MIC	=	25.0	ug.mL-1	PMID[31429278]
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MBC	>	50.0	ug ml-1	PMID[31429278]
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	Ratio	>	2.0	n.a.	PMID[31429278]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC242631 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	21016
0.1-0.2	24052
0.2-0.3	3970
0.3-0.4	638
0.4-0.5	137
0.5-0.6	31
0.6-0.7	7
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7302	Intermediate Similarity	NPC473242
0.7302	Intermediate Similarity	NPC290690
0.7213	Intermediate Similarity	NPC161496
0.6769	Remote Similarity	NPC274330
0.6667	Remote Similarity	NPC51700
0.6667	Remote Similarity	NPC88716
0.6667	Remote Similarity	NPC68160
0.6615	Remote Similarity	NPC17733
0.6615	Remote Similarity	NPC470629
0.6316	Remote Similarity	NPC274507
0.5857	Remote Similarity	NPC126369
0.5857	Remote Similarity	NPC470589
0.5857	Remote Similarity	NPC111110
0.5647	Remote Similarity	NPC211798
0.5634	Remote Similarity	NPC61543
0.5634	Remote Similarity	NPC293048
0.5634	Remote Similarity	NPC225585
0.5556	Remote Similarity	NPC209868
0.5479	Remote Similarity	NPC610635
0.5476	Remote Similarity	NPC607754
0.5417	Remote Similarity	NPC1753
0.5352	Remote Similarity	NPC159365
0.5352	Remote Similarity	NPC198664
0.5342	Remote Similarity	NPC173089
0.5342	Remote Similarity	NPC293564
0.5286	Remote Similarity	NPC30322
0.5278	Remote Similarity	NPC195019
0.527	Remote Similarity	NPC476327
0.5139	Remote Similarity	NPC480946
0.5139	Remote Similarity	NPC187722
0.5139	Remote Similarity	NPC130577
0.5139	Remote Similarity	NPC142415
0.5139	Remote Similarity	NPC102683
0.5135	Remote Similarity	NPC202728
0.5135	Remote Similarity	NPC158059
0.507	Remote Similarity	NPC181225
0.5068	Remote Similarity	NPC182797
0.5068	Remote Similarity	NPC290481
0.5068	Remote Similarity	NPC52169
0.5068	Remote Similarity	NPC488562
0.5068	Remote Similarity	NPC606443

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC242631 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6219
0.1-0.2	2862
0.2-0.3	66
0.3-0.4	2
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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